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Glucose is a sugar with the molecular formula Template:Chem2, which is often abbreviated as Glc.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> It is overall the most abundant monosaccharide,<ref name="DombKost1998">Template:Cite book</ref> a subcategory of carbohydrates. It is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight. It is used by plants to make cellulose, the most abundant carbohydrate in the world, for use in cell walls, and by all living organisms to make adenosine triphosphate (ATP), which is used by the cell as energy.<ref name="froms">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>Template:Cite book</ref><ref name="r2"/>
In energy metabolism, glucose is the most important source of energy in all organisms. Glucose for metabolism is stored as a polymer, in plants mainly as amylose and amylopectin, and in animals as glycogen. Glucose circulates in the blood of animals as blood sugar.<ref name="froms"/><ref name="r2"/> The naturally occurring form is Template:Sm-glucose, while its stereoisomer [[L-glucose|Template:Sm-glucose]] is produced synthetically in comparatively small amounts and is less biologically active.<ref name="r2">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Glucose is a monosaccharide containing six carbon atoms and an aldehyde group, and is therefore an aldohexose. The glucose molecule can exist in an open-chain (acyclic) as well as ring (cyclic) form. Glucose is naturally occurring and is found in its free state in fruits and other parts of plants. In animals, it is released from the breakdown of glycogen in a process known as glycogenolysis.
Glucose, as intravenous sugar solution, is on the World Health Organization's List of Essential Medicines.<ref name="WHO21st">Template:Cite book</ref> It is also on the list in combination with sodium chloride (table salt).<ref name="WHO21st" />
The name glucose is derived from Ancient Greek {{#invoke:Lang|lang}} (Template:Transliteration) 'wine, must', from {{#invoke:Lang|lang}} (Template:Transliteration) 'sweet'.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>Thénard, Gay-Lussac, Biot, and Dumas (1838) "Rapport sur un mémoire de M. Péligiot, intitulé: Recherches sur la nature et les propriétés chimiques des sucres". Template:Webarchive (Report on a memoir of Mr. Péligiot, titled: Investigations on the nature and chemical properties of sugars), Comptes rendus, 7 : 106–113. From page 109. Template:Webarchive: "Il résulte des comparaisons faites par M. Péligot, que le sucre de raisin, celui d'amidon, celui de diabètes et celui de miel ont parfaitement la même composition et les mêmes propriétés, et constituent un seul corps que nous proposons d'appeler Template:Em (1). ... (1) γλευχος, moût, vin doux." It follows from the comparisons made by Mr. Péligot, that the sugar from grapes, that from starch, that from diabetes and that from honey have exactly the same composition and the same properties, and constitute a single substance that we propose to call glucose (1) ... (1) γλευχος, must, sweet wine.</ref> The suffix -ose is a chemical classifier denoting a sugar.
HistoryEdit
Glucose was first isolated from raisins in 1747 by the German chemist Andreas Marggraf.<ref name="Encyclopedia of Food and Health">Template:Cite book</ref><ref>Marggraf (1747) "Experiences chimiques faites dans le dessein de tirer un veritable sucre de diverses plantes, qui croissent dans nos contrées" Template:Webarchive [Chemical experiments made with the intention of extracting real sugar from diverse plants that grow in our lands], Histoire de l'académie royale des sciences et belles-lettres de Berlin, pp. 79–90. From page 90: Template:Webarchive "Les raisins secs, etant humectés d'une petite quantité d'eau, de maniere qu'ils mollissent, peuvent alors etre pilés, & le suc qu'on en exprime, etant depuré & épaissi, fournira une espece de Sucre." ("Raisins, being moistened with a small quantity of water, in a way that they soften, can be then pressed, and the juice that is squeezed out, [after] being purified and thickened, will provide a sort of sugar.")</ref> Glucose was discovered in grapes by another German chemistTemplate:SndJohann Tobias LowitzTemplate:Sndin 1792, and distinguished as being different from cane sugar (sucrose). Glucose is the term coined by Jean Baptiste Dumas in 1838, which has prevailed in the chemical literature. Friedrich August Kekulé proposed the term dextrose (from the Latin {{#invoke:Lang|lang}}, meaning "right"), because in aqueous solution of glucose, the plane of linearly polarized light is turned to the right. In contrast, l-fructose (usually referred to as Template:Sm-fructose) (a ketohexose) and l-glucose (Template:Sm-glucose) turn linearly polarized light to the left. The earlier notation according to the rotation of the plane of linearly polarized light (d and l-nomenclature) was later abandoned in favor of the [[optical rotation#Chirality prefixes|Template:Sm- and Template:Sm-notation]], which refers to the absolute configuration of the asymmetric center farthest from the carbonyl group, and in concordance with the configuration of Template:Sm- or Template:Sm-glyceraldehyde.<ref name="Robyt 7">John F. Robyt: Essentials of Carbohydrate Chemistry. Springer Science & Business Media, 2012, Template:ISBN. p. 7.</ref><ref name="Rosanoff">Template:Cite journal</ref>
Since glucose is a basic necessity of many organisms, a correct understanding of its chemical makeup and structure contributed greatly to a general advancement in organic chemistry. This understanding occurred largely as a result of the investigations of Emil Fischer, a German chemist who received the 1902 Nobel Prize in Chemistry for his findings.<ref>Template:Citation</ref> The synthesis of glucose established the structure of organic material and consequently formed the first definitive validation of Jacobus Henricus van 't Hoff's theories of chemical kinetics and the arrangements of chemical bonds in carbon-bearing molecules.<ref>Template:Citation</ref> Between 1891 and 1894, Fischer established the stereochemical configuration of all the known sugars and correctly predicted the possible isomers, applying Van 't Hoff equation of asymmetrical carbon atoms. The names initially referred to the natural substances. Their enantiomers were given the same name with the introduction of systematic nomenclatures, taking into account absolute stereochemistry (e.g. Fischer nomenclature, Template:Sm/Template:Sm nomenclature).
For the discovery of the metabolism of glucose Otto Meyerhof received the Nobel Prize in Physiology or Medicine in 1922.<ref>"Otto Meyerhof - Facts - NobelPrize.org" Template:Webarchive. NobelPrize.org. Retrieved on 5 September 2018.</ref> Hans von Euler-Chelpin was awarded the Nobel Prize in Chemistry along with Arthur Harden in 1929 for their "research on the fermentation of sugar and their share of enzymes in this process".<ref>"Hans von Euler-Chelpin - Facts - NobelPrize.org" Template:Webarchive. NobelPrize.org. Retrieved on 5 September 2018.</ref><ref>"Arthur Harden - Facts - NobelPrize.org" Template:Webarchive. NobelPrize.org. Retrieved on 5 September 2018.</ref> In 1947, Bernardo Houssay (for his discovery of the role of the pituitary gland in the metabolism of glucose and the derived carbohydrates) as well as Carl and Gerty Cori (for their discovery of the conversion of glycogen from glucose) received the Nobel Prize in Physiology or Medicine.<ref>"Bernardo Houssay - Facts - NobelPrize.org" Template:Webarchive. NobelPrize.org. Retrieved on 5 September 2018.</ref><ref>"Carl Cori - Facts - NobelPrize.org" Template:Webarchive. NobelPrize.org. Retrieved on 5 September 2018.</ref><ref>"Gerty Cori - Facts - NobelPrize.org" Template:Webarchive. NobelPrize.org. Retrieved on 5 September 2018.</ref> In 1970, Luis Leloir was awarded the Nobel Prize in Chemistry for the discovery of glucose-derived sugar nucleotides in the biosynthesis of carbohydrates.<ref>"Luis Leloir - Facts - NobelPrize.org" Template:Webarchive. NobelPrize.org. Retrieved on 5 September 2018.</ref>
Chemical and physical propertiesEdit
Glucose forms white or colorless solids that are highly soluble in water and acetic acid but poorly soluble in methanol and ethanol. They melt at Template:Convert (α) and Template:Convert (beta), decompose starting at Template:Convert with release of various volatile products, ultimately leaving a residue of carbon.<ref name=kang2020>Template:Cite journal</ref> Glucose has a pKa value of 12.16 at Template:Cvt in water.<ref>Template:Cite journal</ref>
With six carbon atoms, it is classed as a hexose, a subcategory of the monosaccharides. Template:Sm-Glucose is one of the sixteen aldohexose stereoisomers. The Template:Sm-isomer, Template:Sm-glucose, also known as dextrose, occurs widely in nature, but the Template:Sm-isomer, [[L-glucose|Template:Sm-glucose]], does not. Glucose can be obtained by hydrolysis of carbohydrates such as milk sugar (lactose), cane sugar (sucrose), maltose, cellulose, glycogen, etc. Dextrose is commonly commercially manufactured from starches, such as corn starch in the US and Japan, from potato and wheat starch in Europe, and from tapioca starch in tropical areas.<ref>Template:Citation</ref> The manufacturing process uses hydrolysis via pressurized steaming at controlled pH in a jet followed by further enzymatic depolymerization.<ref>"glucose." The Columbia Encyclopedia, 6th ed.. 2015. Encyclopedia.com. 17 November 2015 http://www.encyclopedia.com Template:Webarchive.</ref> Unbonded glucose is one of the main ingredients of honey.<ref>Template:Cite journal</ref><ref>Template:Cite journal</ref><ref>Template:Cite book</ref><ref>Template:Cite journal</ref><ref>Template:Cite journal</ref>
The term dextrose is often used in a clinical (related to patient's health status) or nutritional context (related to dietary intake, such as food labels or dietary guidelines), while "glucose" is used in a biological or physiological context (chemical processes and molecular interactions),<ref>Template:Cite journal</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="wid">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> but both terms refer to the same molecule, specifically D-glucose.<ref name="wid"/><ref name="pmid938892">Template:Cite journal</ref>
Dextrose monohydrate is the hydrated form of D-glucose, meaning that it is a glucose molecule with an additional water molecule attached.<ref name="chem"/> Its chemical formula is Template:Chem2 · Template:Chem2.<ref name="chem"/><ref name="api110617">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Dextrose monohydrate is also called hydrated D-glucose, and commonly manufactured from plant starches.<ref name="chem">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="diff">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Dextrose monohydrate is utilized as the predominant type of dextrose in food applications, such as beverage mixes—it is a common form of glucose widely used as a nutrition supplement in production of foodstuffs. Dextrose monohydrate is primarily consumed in North America as a corn syrup or high-fructose corn syrup.<ref name="wid" />
Anhydrous dextrose, on the other hand, is glucose that does not have any water molecules attached to it.<ref name="diff"/><ref name="ahn1">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Anhydrous chemical substances are commonly produced by eliminating water from a hydrated substance through methods such as heating or drying up (desiccation).<ref>Template:Cite journal</ref><ref name="a2">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Dextrose monohydrate can be dehydrated to anhydrous dextrose in industrial setting.<ref>Template:Cite journal</ref><ref>Template:Cite journal</ref> Dextrose monohydrate is composed of approximately 9.5% water by mass; through the process of dehydration, this water content is eliminated to yield anhydrous (dry) dextrose.<ref name="diff"/>
Anhydrous dextrose has the chemical formula Template:Chem2, without any water molecule attached which is the same as glucose.<ref name="chem"/> Anhydrous dextrose on open air tends to absorb moisture and transform to the monohydrate, and it is more expensive to produce.<ref name="diff"/> Anhydrous dextrose (anhydrous D-glucose) has increased stability and increased shelf life,<ref name="a2"/> has medical applications, such as in oral glucose tolerance test.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
Whereas molecular weight (molar mass) for D-glucose monohydrate is 198.17 g/mol,<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> that for anhydrous D-glucose is 180.16 g/mol<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> The density of these two forms of glucose is also different.Template:Specify
In terms of chemical structure, glucose is a monosaccharide, that is, a simple sugar. Glucose contains six carbon atoms and an aldehyde group, and is therefore an aldohexose. The glucose molecule can exist in an open-chain (acyclic) as well as ring (cyclic) form—due to the presence of alcohol and aldehyde or ketone functional groups, the form having the straight chain can easily convert into a chair-like hemiacetal ring structure commonly found in carbohydrates.<ref name="chem2">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
Structure and nomenclatureEdit
Glucose is present in solid form as a monohydrate with a closed pyran ring (α-D-glucopyranose monohydrate, sometimes known less precisely by dextrose hydrate). In aqueous solution, on the other hand, a small proportion of glucose can be found in an open-chain configuration while remaining predominantly as α- or β-pyranose, which interconvert. From aqueous solutions, the three known forms can be crystallized: α-glucopyranose, β-glucopyranose and α-glucopyranose monohydrate.<ref name="Ullmann">Template:Cite book</ref> Glucose is a building block of the disaccharides lactose and sucrose (cane or beet sugar), of oligosaccharides such as raffinose and of polysaccharides such as starch, amylopectin, glycogen, and cellulose.<ref name="r2"/><ref name="pf"/> The glass transition temperature of glucose is Template:Cvt and the Gordon–Taylor constant (an experimentally determined constant for the prediction of the glass transition temperature for different mass fractions of a mixture of two substances)<ref name="pf">Patrick F. Fox: Advanced Dairy Chemistry Volume 3: Lactose, water, salts and vitamins, Springer, 1992. Volume 3, Template:ISBN. p. 316.</ref> is 4.5.<ref name="Caballero 1 76">Benjamin Caballero, Paul Finglas, Fidel Toldrá: Encyclopedia of Food and Health. Academic Press (2016). Template:ISBN, Volume 1, p. 76.</ref>
| Forms and projections of Template:Sm-glucose in comparison | ||
|---|---|---|
| Natta projection | Haworth projection | |
| File:D-Glucose Keilstrich.svg | File:Alpha-D-Glucofuranose.svgTemplate:Pbα-Template:Sm-glucofuranose | File:Beta-D-Glucofuranose.svgTemplate:Pbβ-Template:Sm-glucofuranose |
| File:Alpha-D-Glucopyranose.svgTemplate:Pbα-Template:Sm-glucopyranose | File:Beta-D-Glucopyranose.svgTemplate:Pbβ-Template:Sm-glucopyranose | |
| α-Template:Sm-Glucopyranose in (1) Tollens/Fischer (2) Haworth projection (3) chair conformation (4) Mills projection | ||
| File:Alpha glucose views.svg | ||
Open-chain formEdit
A open-chain form of glucose makes up less than 0.02% of the glucose molecules in an aqueous solution at equilibrium.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> The rest is one of two cyclic hemiacetal forms. In its open-chain form, the glucose molecule has an open (as opposed to cyclic) unbranched backbone of six carbon atoms, where C-1 is part of an aldehyde group Template:Chem2. Therefore, glucose is also classified as an aldose, or an aldohexose. The aldehyde group makes glucose a reducing sugar giving a positive reaction with the Fehling test.
Cyclic formsEdit
Template:Multiple image In solutions, the open-chain form of glucose (either "Template:Small-" or "Template:Small-") exists in equilibrium with several cyclic isomers, each containing a ring of carbons closed by one oxygen atom. In aqueous solution, however, more than 99% of glucose molecules exist as pyranose forms. The open-chain form is limited to about 0.25%, and furanose forms exist in negligible amounts. The terms "glucose" and "Template:Small-glucose" are generally used for these cyclic forms as well. The ring arises from the open-chain form by an intramolecular nucleophilic addition reaction between the aldehyde group (at C-1) and either the C-4 or C-5 hydroxyl group, forming a hemiacetal linkage, Template:Chem2.
The reaction between C-1 and C-5 yields a six-membered heterocyclic system called a pyranose, which is a monosaccharide sugar (hence "-ose") containing a derivatised pyran skeleton. The (much rarer) reaction between C-1 and C-4 yields a five-membered furanose ring, named after the cyclic ether furan. In either case, each carbon in the ring has one hydrogen and one hydroxyl attached, except for the last carbon (C-4 or C-5) where the hydroxyl is replaced by the remainder of the open molecule (which is Template:Chem2 or Template:Chem2 respectively).
The ring-closing reaction can give two products, denoted "α-" and "β-". When a glucopyranose molecule is drawn in the Haworth projection, the designation "α-" means that the hydroxyl group attached to C-1 and the Template:Chem2 group at C-5 lies on opposite sides of the ring's plane (a trans arrangement), while "β-" means that they are on the same side of the plane (a cis arrangement). Therefore, the open-chain isomer Template:Small-glucose gives rise to four distinct cyclic isomers: α-Template:Small-glucopyranose, β-Template:Small-glucopyranose, α-Template:Small-glucofuranose, and β-Template:Small-glucofuranose. These five structures exist in equilibrium and interconvert, and the interconversion is much more rapid with acid catalysis.
The other open-chain isomer Template:Small-glucose similarly gives rise to four distinct cyclic forms of Template:Small-glucose, each the mirror image of the corresponding Template:Small-glucose.
The glucopyranose ring (α or β) can assume several non-planar shapes, analogous to the "chair" and "boat" conformations of cyclohexane. Similarly, the glucofuranose ring may assume several shapes, analogous to the "envelope" conformations of cyclopentane.
In the solid state, only the glucopyranose forms are observed.
Some derivatives of glucofuranose, such as [[1,2-O-isopropylidene-D-glucofuranose|1,2-O-isopropylidene-Template:Sc-glucofuranose]] are stable and can be obtained pure as crystalline solids.<ref name=taka1979>Template:Cite journal</ref><ref name=biel1999>Template:Cite journal</ref> For example, reaction of α-D-glucose with para-tolylboronic acid Template:Chem2 reforms the normal pyranose ring to yield the 4-fold ester α-D-glucofuranose-1,2:3,5-bis(p-tolylboronate).<ref name=chan2006>Template:Cite journal</ref>
MutarotationEdit
Mutarotation consists of a temporary reversal of the ring-forming reaction, resulting in the open-chain form, followed by a reforming of the ring. The ring closure step may use a different Template:Chem2 group than the one recreated by the opening step (thus switching between pyranose and furanose forms), or the new hemiacetal group created on C-1 may have the same or opposite handedness as the original one (thus switching between the α and β forms). Thus, though the open-chain form is barely detectable in solution, it is an essential component of the equilibrium.
The open-chain form is thermodynamically unstable, and it spontaneously isomerizes to the cyclic forms. (Although the ring closure reaction could in theory create four- or three-atom rings, these would be highly strained, and are not observed in practice.) In solutions at room temperature, the four cyclic isomers interconvert over a time scale of hours, in a process called mutarotation.<ref>Template:McMurry2nd.</ref> Starting from any proportions, the mixture converges to a stable ratio of α:β 36:64. The ratio would be α:β 11:89 if it were not for the influence of the anomeric effect.<ref>Template:Citation</ref> Mutarotation is considerably slower at temperatures close to Template:Convert.
Optical activityEdit
Whether in water or the solid form, Template:Sm-(+)-glucose is dextrorotatory, meaning it will rotate the direction of polarized light clockwise as seen looking toward the light source. The effect is due to the chirality of the molecules, and indeed the mirror-image isomer, Template:Sm-(−)-glucose, is levorotatory (rotates polarized light counterclockwise) by the same amount. The strength of the effect is different for each of the five tautomers.
The Template:Sm- prefix does not refer directly to the optical properties of the compound. It indicates that the C-5 chiral centre has the same handedness as that of [[glyceraldehyde|Template:Sm-glyceraldehyde]] (which was so labelled because it is dextrorotatory). The fact that Template:Sm-glucose is dextrorotatory is a combined effect of its four chiral centres, not just of C-5; some of the other Template:Sm-aldohexoses are levorotatory.
The conversion between the two anomers can be observed in a polarimeter since pure α-Template:Sm-glucose has a specific rotation angle of +112.2° mL/(dm·g), pure β-Template:Sm-glucose of +17.5° mL/(dm·g).<ref name=" Hesse">Manfred Hesse, Herbert Meier, Bernd Zeeh, Stefan Bienz, Laurent Bigler, Thomas Fox: Spektroskopische Methoden in der organischen Chemie. 8th revised Edition. Georg Thieme, 2011, Template:ISBN, p. 34 (in German).</ref> When equilibrium has been reached after a certain time due to mutarotation, the angle of rotation is +52.7° mL/(dm·g).<ref name="Hesse" /> By adding acid or base, this transformation is much accelerated. The equilibration takes place via the open-chain aldehyde form.
IsomerisationEdit
In dilute sodium hydroxide or other dilute bases, the monosaccharides mannose, glucose and fructose interconvert (via a Lobry de Bruyn–Alberda–Van Ekenstein transformation), so that a balance between these isomers is formed. This reaction proceeds via an enediol:
Glucose-Fructose-Mannose-isomerisation
Biochemical propertiesEdit
| Metabolism of common monosaccharides and some biochemical reactions of glucose |
|---|
Glucose is the most abundant monosaccharide. Glucose is also the most widely used aldohexose in most living organisms. One possible explanation for this is that glucose has a lower tendency than other aldohexoses to react nonspecifically with the amine groups of proteins.<ref name=Higgins>Template:Cite journal</ref> This reaction—glycation—impairs or destroys the function of many proteins,<ref name=Higgins/> e.g. in glycated hemoglobin. Glucose's low rate of glycation can be attributed to its having a more stable cyclic form compared to other aldohexoses, which means it spends less time than they do in its reactive open-chain form.<ref name=Higgins/> The reason for glucose having the most stable cyclic form of all the aldohexoses is that its hydroxy groups (with the exception of the hydroxy group on the anomeric carbon of Template:Sm-glucose) are in the equatorial position. Presumably, glucose is the most abundant natural monosaccharide because it is less glycated with proteins than other monosaccharides.<ref name=Higgins /><ref name="Stryer 531">Jeremy M. Berg: Stryer Biochemie Template:In lang. Springer-Verlag, 2017, Template:ISBN, p. 531.</ref> Another hypothesis is that glucose, being the only Template:Sm-aldohexose that has all five hydroxy substituents in the equatorial position in the form of β-Template:Sm-glucose, is more readily accessible to chemical reactions,<ref name="Garrett">Template:Cite book</ref>Template:Rp for example, for esterification<ref name=Voet>Template:Cite book</ref>Template:Rp or acetal formation.<ref>Albert L. Lehninger, Biochemistry, 6th printing, Worth Publishers Inc. 1972, Template:ISBN p. 228.</ref> For this reason, Template:Sm-glucose is also a highly preferred building block in natural polysaccharides (glycans). Polysaccharides that are composed solely of glucose are termed glucans.
Glucose is produced by plants through photosynthesis using sunlight,<ref name="photo"/><ref name="Löffler/Petrides 195"/> water and carbon dioxide and can be used by all living organisms as an energy and carbon source. However, most glucose does not occur in its free form, but in the form of its polymers, i.e. lactose, sucrose, starch and others which are energy reserve substances, and cellulose and chitin, which are components of the cell wall in plants or fungi and arthropods, respectively. These polymers, when consumed by animals, fungi and bacteria, are degraded to glucose using enzymes. All animals are also able to produce glucose themselves from certain precursors as the need arises. Neurons, cells of the renal medulla and erythrocytes depend on glucose for their energy production.<ref name="Löffler/Petrides 195">Peter C. Heinrich: Löffler/Petrides Biochemie und Pathobiochemie Template:In lang.. Springer-Verlag, 2014, Template:ISBN, p. 195.</ref> In adult humans, there is about Template:Cvt of glucose,<ref name="Satyanarayana">U. Satyanarayana: Biochemistry. Elsevier Health Sciences, 2014, Template:ISBN. p. 674.</ref> of which about Template:Cvt is present in the blood.<ref>Template:Cite journal</ref> Approximately Template:Cvt of glucose is produced in the liver of an adult in 24 hours.<ref name="Satyanarayana" />
Many of the long-term complications of diabetes (e.g., blindness, kidney failure, and peripheral neuropathy) are probably due to the glycation of proteins or lipids.<ref>Template:Citation</ref> In contrast, enzyme-regulated addition of sugars to protein is called glycosylation and is essential for the function of many proteins.<ref name="varki">Template:Cite book</ref>
UptakeEdit
Ingested glucose initially binds to the receptor for sweet taste on the tongue in humans. This complex of the proteins T1R2 and T1R3 makes it possible to identify glucose-containing food sources.<ref name="fca">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="Löffler/Petrides 404"/> Glucose mainly comes from food—about Template:Cvt per day is produced by conversion of food,<ref name="Löffler/Petrides 404">Peter C. Heinrich: Löffler/Petrides Biochemie und Pathobiochemie. Springer-Verlag, 2014, Template:ISBN, p. 404.</ref> but it is also synthesized from other metabolites in the body's cells. In humans, the breakdown of glucose-containing polysaccharides happens in part already during chewing by means of amylase, which is contained in saliva, as well as by maltase, lactase, and sucrase on the brush border of the small intestine. Glucose is a building block of many carbohydrates and can be split off from them using certain enzymes. Glucosidases, a subgroup of the glycosidases, first catalyze the hydrolysis of long-chain glucose-containing polysaccharides, removing terminal glucose. In turn, disaccharides are mostly degraded by specific glycosidases to glucose. The names of the degrading enzymes are often derived from the particular poly- and disaccharide; inter alia, for the degradation of polysaccharide chains there are amylases (named after amylose, a component of starch), cellulases (named after cellulose), chitinases (named after chitin), and more. Furthermore, for the cleavage of disaccharides, there are maltase, lactase, sucrase, trehalase, and others. In humans, about 70 genes are known that code for glycosidases. They have functions in the digestion and degradation of glycogen, sphingolipids, mucopolysaccharides, and poly(ADP-ribose). Humans do not produce cellulases, chitinases, or trehalases, but the bacteria in the gut microbiota do.
In order to get into or out of cell membranes of cells and membranes of cell compartments, glucose requires special transport proteins from the major facilitator superfamily. In the small intestine (more precisely, in the jejunum),<ref name="Harper 641">Harold A. Harper: Medizinische Biochemie Template:In lang. Springer-Verlag, 2013, Template:ISBN, p. 641.</ref> glucose is taken up into the intestinal epithelium with the help of glucose transporters<ref>Template:Cite journal</ref> via a secondary active transport mechanism called sodium ion-glucose symport via sodium/glucose cotransporter 1 (SGLT1).<ref name="Löffler/Petrides 199" /> Further transfer occurs on the basolateral side of the intestinal epithelial cells via the glucose transporter GLUT2,<ref name="Löffler/Petrides 199" /> as well uptake into liver cells, kidney cells, cells of the islets of Langerhans, neurons, astrocytes, and tanycytes.<ref>Template:Cite journal</ref> Glucose enters the liver via the portal vein and is stored there as a cellular glycogen.<ref name="Löffler/Petrides 214" /> In the liver cell, it is phosphorylated by glucokinase at position 6 to form glucose 6-phosphate, which cannot leave the cell. Glucose 6-phosphatase can convert glucose 6-phosphate back into glucose exclusively in the liver, so the body can maintain a sufficient blood glucose concentration. In other cells, uptake happens by passive transport through one of the 14 GLUT proteins.<ref name="Löffler/Petrides 199" /> In the other cell types, phosphorylation occurs through a hexokinase, whereupon glucose can no longer diffuse out of the cell.
The glucose transporter GLUT1 is produced by most cell types and is of particular importance for nerve cells and pancreatic β-cells.<ref name="Löffler/Petrides 199" /> GLUT3 is highly expressed in nerve cells.<ref name="Löffler/Petrides 199" /> Glucose from the bloodstream is taken up by GLUT4 from muscle cells (of the skeletal muscle<ref>Template:Cite journal</ref> and heart muscle) and fat cells.<ref>Template:Cite book</ref> GLUT14 is expressed exclusively in testicles.<ref>Template:Cite journal</ref> Excess glucose is broken down and converted into fatty acids, which are stored as triglycerides. In the kidneys, glucose in the urine is absorbed via SGLT1 and SGLT2 in the apical cell membranes and transmitted via GLUT2 in the basolateral cell membranes.<ref>Template:Cite journal</ref> About 90% of kidney glucose reabsorption is via SGLT2 and about 3% via SGLT1.<ref>Template:Cite journal</ref>
BiosynthesisEdit
{{#invoke:Labelled list hatnote|labelledList|Main article|Main articles|Main page|Main pages}} In plants and some prokaryotes, glucose is a product of photosynthesis.<ref name="photo">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Glucose is also formed by the breakdown of polymeric forms of glucose like glycogen (in animals and mushrooms) or starch (in plants). The cleavage of glycogen is termed glycogenolysis, the cleavage of starch is called starch degradation.<ref>Template:Cite journal</ref>
The metabolic pathway that begins with molecules containing two to four carbon atoms (C) and ends in the glucose molecule containing six carbon atoms is called gluconeogenesis and occurs in all living organisms. The smaller starting materials are the result of other metabolic pathways. Ultimately almost all biomolecules come from the assimilation of carbon dioxide in plants and microbes during photosynthesis.<ref name=Voet/>Template:Rp The free energy of formation of α-Template:Sm-glucose is 917.2 kilojoules per mole.<ref name=Voet/>Template:Rp In humans, gluconeogenesis occurs in the liver and kidney,<ref name="Szablewski">Leszek Szablewski: Glucose Homeostasis and Insulin Resistance. Bentham Science Publishers, 2011, Template:ISBN, p. 46.</ref> but also in other cell types. In the liver about Template:Cvt of glycogen are stored, in skeletal muscle about Template:Cvt.<ref name="Löffler/Petrides 389">Peter C. Heinrich: Löffler/Petrides Biochemie und Pathobiochemie Template:In lang. Springer-Verlag, 2014, Template:ISBN, p. 389.</ref> However, the glucose released in muscle cells upon cleavage of the glycogen can not be delivered to the circulation because glucose is phosphorylated by the hexokinase, and a glucose-6-phosphatase is not expressed to remove the phosphate group. Unlike for glucose, there is no transport protein for glucose-6-phosphate. Gluconeogenesis allows the organism to build up glucose from other metabolites, including lactate or certain amino acids, while consuming energy. The renal tubular cells can also produce glucose.
Glucose also can be found outside of living organisms in the ambient environment. Glucose concentrations in the atmosphere are detected via collection of samples by aircraft and are known to vary from location to location. For example, glucose concentrations in atmospheric air from inland China range from 0.8 to 20.1 pg/L, whereas east coastal China glucose concentrations range from 10.3 to 142 pg/L.<ref>Template:Cite journal</ref>
Glucose degradationEdit
{{#invoke:Labelled list hatnote|labelledList|Main article|Main articles|Main page|Main pages}}
In humans, glucose is metabolized by glycolysis<ref>Template:Cite journal</ref> and the pentose phosphate pathway.<ref name="Horton">H. Robert Horton, Laurence A. Moran, K. Gray Scrimgeour, Marc D. Perry, J. David Rawn: Biochemie Template:In lang. Pearson Studium; 4. aktualisierte Auflage 2008; Template:ISBN; pp. 490–496.</ref> Glycolysis is used by all living organisms,<ref name="Garrett"/>Template:Rp<ref name="Hall">Brian K. Hall: Strickberger's Evolution. Jones & Bartlett Publishers, 2013, Template:ISBN, p. 164.</ref> with small variations, and all organisms generate energy from the breakdown of monosaccharides.<ref name="Hall" /> In the further course of the metabolism, it can be completely degraded via oxidative decarboxylation, the citric acid cycle (synonym Krebs cycle) and the respiratory chain to water and carbon dioxide. If there is not enough oxygen available for this, the glucose degradation in animals occurs anaerobic to lactate via lactic acid fermentation and releases much less energy. Muscular lactate enters the liver through the bloodstream in mammals, where gluconeogenesis occurs (Cori cycle). With a high supply of glucose, the metabolite acetyl-CoA from the Krebs cycle can also be used for fatty acid synthesis.<ref>Template:Cite journal</ref> Glucose is also used to replenish the body's glycogen stores, which are mainly found in liver and skeletal muscle. These processes are hormonally regulated.
In other living organisms, other forms of fermentation can occur. The bacterium Escherichia coli can grow on nutrient media containing glucose as the sole carbon source.<ref name=Voet/>Template:Rp In some bacteria and, in modified form, also in archaea, glucose is degraded via the Entner-Doudoroff pathway.<ref>Template:Cite journal</ref> With glucose, a mechanism for gene regulation was discovered in E. coli, the catabolite repression (formerly known as glucose effect).<ref name="PMID29330542">Template:Cite journal</ref>
Use of glucose as an energy source in cells is by either aerobic respiration, anaerobic respiration, or fermentation.<ref name="sil"/> The first step of glycolysis is the phosphorylation of glucose by a hexokinase to form glucose 6-phosphate. The main reason for the immediate phosphorylation of glucose is to prevent its diffusion out of the cell as the charged phosphate group prevents glucose 6-phosphate from easily crossing the cell membrane.<ref name="sil">Template:Cite journal</ref> Furthermore, addition of the high-energy phosphate group activates glucose for subsequent breakdown in later steps of glycolysis.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
In anaerobic respiration, one glucose molecule produces a net gain of two ATP molecules (four ATP molecules are produced during glycolysis through substrate-level phosphorylation, but two are required by enzymes used during the process).<ref>Template:Citation</ref> In aerobic respiration, a molecule of glucose is much more profitable in that a maximum net production of 30 or 32 ATP molecules (depending on the organism) is generated.<ref>Template:Citation</ref>
Template:GlycolysisGluconeogenesis WP534
Tumor cells often grow comparatively quickly and consume an above-average amount of glucose by glycolysis,<ref>Template:Cite journal</ref> which leads to the formation of lactate, the end product of fermentation in mammals, even in the presence of oxygen. This is called the Warburg effect. For the increased uptake of glucose in tumors various SGLT and GLUT are overly produced.<ref>Template:Cite journal</ref><ref>Template:Cite journal</ref>
In yeast, ethanol is fermented at high glucose concentrations, even in the presence of oxygen (which normally leads to respiration rather than fermentation). This is called the Crabtree effect.
Glucose can also degrade to form carbon dioxide through abiotic means. This has been demonstrated to occur experimentally via oxidation and hydrolysis at 22 °C and a pH of 2.5.<ref>Template:Cite journal</ref>
Energy sourceEdit
Glucose is a ubiquitous fuel in biology. It is used as an energy source in organisms, from bacteria to humans, through either aerobic respiration, anaerobic respiration (in bacteria), or fermentation. Glucose is the human body's key source of energy, through aerobic respiration, providing about 3.75 kilocalories (16 kilojoules) of food energy per gram.<ref>Template:Citation</ref> Breakdown of carbohydrates (e.g., starch) yields mono- and disaccharides, most of which is glucose. Through glycolysis and later in the reactions of the citric acid cycle and oxidative phosphorylation, glucose is oxidized to eventually form carbon dioxide and water, yielding energy mostly in the form of adenosine triphosphate (ATP). The insulin reaction, and other mechanisms, regulate the concentration of glucose in the blood. The physiological caloric value of glucose, depending on the source, is 16.2 kilojoules per gram<ref name="Schwedt">Georg Schwedt: Zuckersüße Chemie Template:In lang. John Wiley & Sons, 2012, Template:ISBN, p. 100.</ref> or 15.7 kJ/g (3.74 kcal/g).<ref>Schmidt, Lang: Physiologie des Menschen, 30. Auflage. Springer Verlag, 2007, p. 907 Template:In lang.</ref> The high availability of carbohydrates from plant biomass has led to a variety of methods during evolution, especially in microorganisms, to utilize glucose for energy and carbon storage. Differences exist in which end product can no longer be used for energy production. The presence of individual genes, and their gene products, the enzymes, determine which reactions are possible. The metabolic pathway of glycolysis is used by almost all living beings. An essential difference in the use of glycolysis is the recovery of NADPH as a reductant for anabolism that would otherwise have to be generated indirectly.<ref>Template:Cite journal</ref>
Glucose and oxygen supply almost all the energy for the brain,<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> so its availability influences psychological processes. When glucose is low, psychological processes requiring mental effort (e.g., self-control, effortful decision-making) are impaired.<ref>Template:Citation</ref><ref>Template:Citation</ref><ref>Template:Citation</ref><ref>Template:Citation</ref> In the brain, which is dependent on glucose and oxygen as the major source of energy, the glucose concentration is usually 4 to 6 mM (5 mM equals 90 mg/dL),<ref name="Satyanarayana" /> but decreases to 2 to 3 mM when fasting.<ref name="Dwyer" /> Confusion occurs below 1 mM and coma at lower levels.<ref name="Dwyer" />
The glucose in the blood is called blood sugar. Blood sugar levels are regulated by glucose-binding nerve cells in the hypothalamus.<ref name="Koekkoek">Template:Cite journal</ref> In addition, glucose in the brain binds to glucose receptors of the reward system in the nucleus accumbens.<ref name="Koekkoek" /> The binding of glucose to the sweet receptor on the tongue induces a release of various hormones of energy metabolism, either through glucose or through other sugars, leading to an increased cellular uptake and lower blood sugar levels.<ref name="Tucker">Template:Cite journal</ref> Artificial sweeteners do not lower blood sugar levels.<ref name="Tucker" />
The blood sugar content of a healthy person in the short-time fasting state, e.g. after overnight fasting, is about 70 to 100 mg/dL of blood (4 to 5.5 mM). In blood plasma, the measured values are about 10–15% higher. In addition, the values in the arterial blood are higher than the concentrations in the venous blood since glucose is absorbed into the tissue during the passage of the capillary bed. Also in the capillary blood, which is often used for blood sugar determination, the values are sometimes higher than in the venous blood. The glucose content of the blood is regulated by the hormones insulin, incretin and glucagon.<ref name="Koekkoek" /><ref>Template:Cite book.</ref> Insulin lowers the glucose level, glucagon increases it.<ref name="Satyanarayana" /> Furthermore, the hormones adrenaline, thyroxine, glucocorticoids, somatotropin and adrenocorticotropin lead to an increase in the glucose level.<ref name="Satyanarayana" /> There is also a hormone-independent regulation, which is referred to as glucose autoregulation.<ref>Template:Cite journal</ref> After food intake the blood sugar concentration increases. Values over 180 mg/dL in venous whole blood are pathological and are termed hyperglycemia, values below 40 mg/dL are termed hypoglycaemia.<ref>W. A. Scherbaum, B. M. Lobnig, In: Hans-Peter Wolff, Thomas R. Weihrauch: Internistische Therapie 2006, 2007. 16th Edition. Elsevier, 2006, Template:ISBN, p. 927, 985 Template:In lang.</ref> When needed, glucose is released into the bloodstream by glucose-6-phosphatase from glucose-6-phosphate originating from liver and kidney glycogen, thereby regulating the homeostasis of blood glucose concentration.<ref name="Szablewski" /><ref name="Löffler/Petrides 195" /> In ruminants, the blood glucose concentration is lower (60 mg/dL in cattle and 40 mg/dL in sheep), because the carbohydrates are converted more by their gut microbiota into short-chain fatty acids.<ref name="Harper">Harold A. Harper: Medizinische Biochemie. Springer-Verlag, 2013, Template:ISBN, p. 294.</ref>
Some glucose is converted to lactic acid by astrocytes, which is then utilized as an energy source by brain cells; some glucose is used by intestinal cells and red blood cells, while the rest reaches the liver, adipose tissue and muscle cells, where it is absorbed and stored as glycogen (under the influence of insulin). Liver cell glycogen can be converted to glucose and returned to the blood when insulin is low or absent; muscle cell glycogen is not returned to the blood because of a lack of enzymes. In fat cells, glucose is used to power reactions that synthesize some fat types and have other purposes. Glycogen is the body's "glucose energy storage" mechanism, because it is much more "space efficient" and less reactive than glucose itself.
As a result of its importance in human health, glucose is an analyte in glucose tests that are common medical blood tests.<ref>Template:Cite journal</ref> Eating or fasting prior to taking a blood sample has an effect on analyses for glucose in the blood; a high fasting glucose blood sugar level may be a sign of prediabetes or diabetes mellitus.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
The glycemic index is an indicator of the speed of resorption and conversion to blood glucose levels from ingested carbohydrates, measured as the area under the curve of blood glucose levels after consumption in comparison to glucose (glucose is defined as 100).<ref name="Harvey 366">Richard A. Harvey, Denise R. Ferrier: Biochemistry. 5th Edition, Lippincott Williams & Wilkins, 2011, Template:ISBN, p. 366.</ref> The clinical importance of the glycemic index is controversial,<ref name="Harvey 366" /><ref name="Satyarayana 508">U Satyanarayana: Biochemistry. Elsevier Health Sciences, 2014, Template:ISBN, p. 508.</ref> as foods with high fat contents slow the resorption of carbohydrates and lower the glycemic index, e.g. ice cream.<ref name="Satyarayana 508" /> An alternative indicator is the insulin index,<ref>Template:Cite journal</ref> measured as the impact of carbohydrate consumption on the blood insulin levels. The glycemic load is an indicator for the amount of glucose added to blood glucose levels after consumption, based on the glycemic index and the amount of consumed food.
PrecursorEdit
Organisms use glucose as a precursor for the synthesis of several important substances. Starch, cellulose, and glycogen ("animal starch") are common glucose polymers (polysaccharides). Some of these polymers (starch or glycogen) serve as energy stores, while others (cellulose and chitin, which is made from a derivative of glucose) have structural roles. Oligosaccharides of glucose combined with other sugars serve as important energy stores. These include lactose, the predominant sugar in milk, which is a glucose-galactose disaccharide, and sucrose, another disaccharide which is composed of glucose and fructose. Glucose is also added onto certain proteins and lipids in a process called glycosylation. This is often critical for their functioning. The enzymes that join glucose to other molecules usually use phosphorylated glucose to power the formation of the new bond by coupling it with the breaking of the glucose-phosphate bond.
Other than its direct use as a monomer, glucose can be broken down to synthesize a wide variety of other biomolecules. This is important, as glucose serves both as a primary store of energy and as a source of organic carbon. Glucose can be broken down and converted into lipids. It is also a precursor for the synthesis of other important molecules such as vitamin C (ascorbic acid). In living organisms, glucose is converted to several other chemical compounds that are the starting material for various metabolic pathways. Among them, all other monosaccharides<ref name="Löffler/Petrides 27">Peter C. Heinrich: Löffler/Petrides Biochemie und Pathobiochemie Template:In lang. Springer-Verlag, 2014, Template:ISBN, p. 27.</ref> such as fructose (via the polyol pathway),<ref name="Löffler/Petrides 199">Peter C. Heinrich: Löffler/Petrides Biochemie und Pathobiochemie Template:In lang. Springer-Verlag, 2014, Template:ISBN, p. 199, 200.</ref> mannose (the epimer of glucose at position 2), galactose (the epimer at position 4), fucose, various uronic acids and the amino sugars are produced from glucose.<ref name="Löffler/Petrides 214">Peter C. Heinrich: Löffler/Petrides Biochemie und Pathobiochemie Template:In lang. Springer-Verlag, 2014, Template:ISBN, p. 214.</ref> In addition to the phosphorylation to glucose-6-phosphate, which is part of the glycolysis, glucose can be oxidized during its degradation to glucono-1,5-lactone. Glucose is used in some bacteria as a building block in the trehalose or the dextran biosynthesis and in animals as a building block of glycogen. Glucose can also be converted from bacterial xylose isomerase to fructose. In addition, glucose metabolites produce all nonessential amino acids, sugar alcohols such as mannitol and sorbitol, fatty acids, cholesterol and nucleic acids.<ref name="Löffler/Petrides 27" /> Finally, glucose is used as a building block in the glycosylation of proteins to glycoproteins, glycolipids, peptidoglycans, glycosides and other substances (catalyzed by glycosyltransferases) and can be cleaved from them by glycosidases.
Regulatory role in cell differentiationEdit
In addition to its well-known function as a cellular energy source, glucose has been identified as a master regulator of tissue maturation.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> A 2025 study by Stanford Medicine uncovered that glucose, in its intact (non-metabolized) form, can bind to various regulatory proteins involved in gene expression. One such protein is IRF6, which alters its conformation upon glucose binding, thereby influencing the expression of genes associated with stem cell differentiation. This regulatory role is independent of glucose’s catabolic function and has been observed across multiple tissue types, including skin, bone, fat, and white blood cells. The research demonstrated that even glucose analogs incapable of metabolism could promote differentiation, suggesting a signaling function for glucose. These findings have potential implications in understanding and treating diseases characterized by impaired differentiation, such as diabetes and certain cancers.<ref>Template:Cite journal</ref>
PathologyEdit
DiabetesEdit
Diabetes is a metabolic disorder where the body is unable to regulate levels of glucose in the blood either because of a lack of insulin in the body or the failure, by cells in the body, to respond properly to insulin. Each of these situations can be caused by persistently high elevations of blood glucose levels, through pancreatic burnout and insulin resistance. The pancreas is the organ responsible for the secretion of the hormones insulin and glucagon.<ref>Template:Cite journal</ref> Insulin is a hormone that regulates glucose levels, allowing the body's cells to absorb and use glucose. Without it, glucose cannot enter the cell and therefore cannot be used as fuel for the body's functions.<ref>Estela, Carlos (2011) "Blood Glucose Levels," Undergraduate Journal of Mathematical Modeling: One + Two: Vol. 3: Iss. 2, Article 12.</ref> If the pancreas is exposed to persistently high elevations of blood glucose levels, the insulin-producing cells in the pancreas could be damaged, causing a lack of insulin in the body. Insulin resistance occurs when the pancreas tries to produce more and more insulin in response to persistently elevated blood glucose levels. Eventually, the rest of the body becomes resistant to the insulin that the pancreas is producing, thereby requiring more insulin to achieve the same blood glucose-lowering effect, and forcing the pancreas to produce even more insulin to compete with the resistance. This negative spiral contributes to pancreatic burnout, and the disease progression of diabetes.
To monitor the body's response to blood glucose-lowering therapy, glucose levels can be measured. Blood glucose monitoring can be performed by multiple methods, such as the fasting glucose test which measures the level of glucose in the blood after 8 hours of fasting. Another test is the 2-hour glucose tolerance test (GTT)Template:Sndfor this test, the person has a fasting glucose test done, then drinks a 75-gram glucose drink and is retested. This test measures the ability of the person's body to process glucose. Over time the blood glucose levels should decrease as insulin allows it to be taken up by cells and exit the blood stream.
Hypoglycemia managementEdit
Individuals with diabetes or other conditions that result in low blood sugar often carry small amounts of sugar in various forms. One sugar commonly used is glucose, often in the form of glucose tablets (glucose pressed into a tablet shape sometimes with one or more other ingredients as a binder), hard candy, or sugar packet.
SourcesEdit
Most dietary carbohydrates contain glucose, either as their only building block (as in the polysaccharides starch and glycogen), or together with another monosaccharide (as in the hetero-polysaccharides sucrose and lactose).<ref>Template:Cite news</ref> Unbound glucose is one of the main ingredients of honey. Glucose is extremely abundant and has been isolated from a variety of natural sources across the world, including male cones of the coniferous tree Wollemia nobilis in Rome,<ref>Template:Cite journal</ref> the roots of Ilex asprella plants in China,<ref>Template:Cite journal</ref> and straws from rice in California.<ref>Template:Cite book</ref>
| CitationClass=web
}}</ref> | |||||||
| Food item |
Carbohydrate, total,Template:Efn including dietary fiber |
Total sugars |
Free fructose |
Free glucose |
Sucrose | Ratio of fructose/ glucose |
Sucrose as proportion of total sugars (%) |
|---|---|---|---|---|---|---|---|
| Fruits | |||||||
| Apple | 13.8 | 10.4 | 5.9 | 2.4 | 2.1 | 2.0 | 19.9 |
| Apricot | 11.1 | 9.2 | 0.9 | 2.4 | 5.9 | 0.7 | 63.5 |
| Banana | 22.8 | 12.2 | 4.9 | 5.0 | 2.4 | 1.0 | 20.0 |
| Fig, dried | 63.9 | 47.9 | 22.9 | 24.8 | 0.9 | 0.93 | 0.15 |
| Grapes | 18.1 | 15.5 | 8.1 | 7.2 | 0.2 | 1.1 | 1 |
| Navel orange | 12.5 | 8.5 | 2.25 | 2.0 | 4.3 | 1.1 | 50.4 |
| Peach | 9.5 | 8.4 | 1.5 | 2.0 | 4.8 | 0.9 | 56.7 |
| Pear | 15.5 | 9.8 | 6.2 | 2.8 | 0.8 | 2.1 | 8.0 |
| Pineapple | 13.1 | 9.9 | 2.1 | 1.7 | 6.0 | 1.1 | 60.8 |
| Plum | 11.4 | 9.9 | 3.1 | 5.1 | 1.6 | 0.66 | 16.2 |
| Vegetables | |||||||
| Beet, red | 9.6 | 6.8 | 0.1 | 0.1 | 6.5 | 1.0 | 96.2 |
| Carrot | 9.6 | 4.7 | 0.6 | 0.6 | 3.6 | 1.0 | 77 |
| Red pepper, sweet | 6.0 | 4.2 | 2.3 | 1.9 | 0.0 | 1.2 | 0.0 |
| Onion, sweet | 7.6 | 5.0 | 2.0 | 2.3 | 0.7 | 0.9 | 14.3 |
| Sweet potato | 20.1 | 4.2 | 0.7 | 1.0 | 2.5 | 0.9 | 60.3 |
| Yam | 27.9 | 0.5 | Template:N/a | Template:N/a | Template:N/a | Template:N/a | Template:N/a |
| Sugar cane | 13–18 | 0.2–1.0 | 0.2–1.0 | 11–16 | 1.0 | high | |
| Sugar beet | 17–18 | 0.1–0.5 | 0.1–0.5 | 16–17 | 1.0 | high | |
| Grains | |||||||
| Corn, sweet | 19.0 | 6.2 | 1.9 | 3.4 | 0.9 | 0.61 | 15.0 |
Commercial productionEdit
Glucose is produced industrially from starch by enzymatic hydrolysis using glucose amylase or by the use of acids. Enzymatic hydrolysis has largely displaced acid-catalyzed hydrolysis reactions.<ref name="Fellows">P. J. Fellows: Food Processing Technology. Woodhead Publishing, 2016, Template:ISBN, p. 197.</ref> The result is glucose syrup (enzymatically with more than 90% glucose in the dry matter)<ref name="Fellows" /> with an annual worldwide production volume of 20 million tonnes (as of 2011).<ref name="Ullmann 48">Thomas Becker, Dietmar Breithaupt, Horst Werner Doelle, Armin Fiechter, Günther Schlegel, Sakayu Shimizu, Hideaki Yamada: Biotechnology, in: Ullmann's Encyclopedia of Industrial Chemistry, 7th Edition, Wiley-VCH, 2011. Template:ISBN. Volume 6, p. 48.</ref> This is the reason for the former common name "starch sugar". The amylases most often come from Bacillus licheniformis<ref name="ResSoc">The Amylase Research Society of Japan: Handbook of Amylases and Related Enzymes. Elsevier, 2014, Template:ISBN, p. 195.</ref> or Bacillus subtilis (strain MN-385),<ref name="ResSoc" /> which are more thermostable than the originally used enzymes.<ref name="ResSoc" /><ref name="Madsen">Template:Cite journal</ref> Starting in 1982, pullulanases from Aspergillus niger were used in the production of glucose syrup to convert amylopectin to starch (amylose), thereby increasing the yield of glucose.<ref name="Norman">Template:Cite journal</ref> The reaction is carried out at a pH = 4.6–5.2 and a temperature of 55–60 °C.<ref name="Encyclopedia of Food and Health" /> Corn syrup has between 20% and 95% glucose in the dry matter.<ref>Template:Cite book</ref><ref>Template:Cite book</ref> The Japanese form of the glucose syrup, Mizuame, is made from sweet potato or rice starch.<ref>Alan Davidson: Oxford Companion to Food (1999). "Mizuame", p. 510 Template:ISBN.</ref>
Many crops can be used as the source of starch. Maize,<ref name="Fellows" /> rice,<ref name="Fellows" /> wheat,<ref name="Fellows" /> cassava,<ref name="Fellows" /> potato,<ref name="Fellows" /> barley,<ref name="Fellows" /> sweet potato,<ref name="Davidson">Alan Davidson: The Oxford Companion to Food. OUP Oxford, 2014, Template:ISBN, p. 527.</ref> corn husk and sago are all used in various parts of the world. In the United States, corn starch (from maize) is used almost exclusively. Some commercial glucose occurs as a component of invert sugar, a roughly 1:1 mixture of glucose and fructose that is produced from sucrose. In principle, cellulose could be hydrolyzed to glucose, but this process is not yet commercially practical.<ref name="Ullmann" />
Conversion to fructoseEdit
{{#invoke:Labelled list hatnote|labelledList|Main article|Main articles|Main page|Main pages}} In the US, almost exclusively corn (more precisely, corn syrup) is used as glucose source for the production of isoglucose, which is a mixture of glucose and fructose, since fructose has a higher sweetening powerTemplate:Sndwith same physiological calorific value of 374 kilocalories per 100 g. The annual world production of isoglucose is 8 million tonnes (as of 2011).<ref name="Ullmann 48" /> When made from corn syrup, the final product is high-fructose corn syrup (HFCS).
Commercial usageEdit
Glucose is mainly used for the production of fructose and of glucose-containing foods. In foods, it is used as a sweetener, humectant, to increase the volume and to create a softer mouthfeel.<ref name="Fellows" /> Various sources of glucose, such as grape juice (for wine) or malt (for beer), are used for fermentation to ethanol during the production of alcoholic beverages. Most soft drinks in the US use HFCS-55 (with a fructose content of 55% in the dry mass), while most other HFCS-sweetened foods in the US use HFCS-42 (with a fructose content of 42% in the dry mass).<ref name="fda2014">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> In Mexico, on the other hand, soft drinks are sweetened by cane sugar, which has a higher sweetening power.<ref>Kevin Pang: "Mexican Coke a Hit in U.S." In: Seattle Times, 29 October 2004.</ref> In addition, glucose syrup is used, inter alia, in the production of confectionery such as candies, toffee and fondant.<ref name="Beckett">Steve T. Beckett: Beckett's Industrial Chocolate Manufacture and Use. John Wiley & Sons, 2017, Template:ISBN, p. 82.</ref> Typical chemical reactions of glucose when heated under water-free conditions are caramelization and, in presence of amino acids, the Maillard reaction.
In addition, various organic acids can be biotechnologically produced from glucose, for example by fermentation with Clostridium thermoaceticum to produce acetic acid, with Penicillium notatum for the production of araboascorbic acid, with Rhizopus delemar for the production of fumaric acid, with Aspergillus niger for the production of gluconic acid, with Candida brumptii to produce isocitric acid, with Aspergillus terreus for the production of itaconic acid, with Pseudomonas fluorescens for the production of 2-ketogluconic acid, with Gluconobacter suboxydans for the production of 5-ketogluconic acid, with Aspergillus oryzae for the production of kojic acid, with Lactobacillus delbrueckii for the production of lactic acid, with Lactobacillus brevis for the production of malic acid, with Propionibacter shermanii for the production of propionic acid, with Pseudomonas aeruginosa for the production of pyruvic acid and with Gluconobacter suboxydans for the production of tartaric acid.<ref name="Kent">James A. Kent: Riegel's Handbook of Industrial Chemistry. Springer Science & Business Media, 2013, Template:ISBN, p. 938.</ref>Template:Additional citation needed Potent, bioactive natural products like triptolide that inhibit mammalian transcription via inhibition of the XPB subunit of the general transcription factor TFIIH has been recently reported as a glucose conjugate for targeting hypoxic cancer cells with increased glucose transporter expression.<ref>Template:Cite journal</ref> Recently, glucose has been gaining commercial use as a key component of "kits" containing lactic acid and insulin intended to induce hypoglycemia and hyperlactatemia to combat different cancers and infections.<ref>Template:Cite journal</ref>
AnalysisEdit
When a glucose molecule is to be detected at a certain position in a larger molecule, nuclear magnetic resonance spectroscopy, X-ray crystallography analysis or lectin immunostaining is performed with concanavalin A reporter enzyme conjugate, which binds only glucose or mannose.
Classical qualitative detection reactionsEdit
These reactions have only historical significance:
Fehling testEdit
The Fehling test is a classic method for the detection of aldoses.<ref name="Fehling-Harn">H. Fehling: Quantitative Bestimmung des Zuckers im Harn. In: Archiv für physiologische Heilkunde (1848), volume 7, p. 64–73 (in German).</ref> Due to mutarotation, glucose is always present to a small extent as an open-chain aldehyde. By adding the Fehling reagents (Fehling (I) solution and Fehling (II) solution), the aldehyde group is oxidized to a carboxylic acid, while the Cu2+ tartrate complex is reduced to Cu+ and forms a brick red precipitate (Cu2O).
Tollens testEdit
In the Tollens test, after addition of ammoniacal AgNO3 to the sample solution, glucose reduces Ag+ to elemental silver.<ref>B. Tollens: Über ammon-alkalische Silberlösung als Reagens auf Aldehyd Template:Webarchive. In Berichte der Deutschen Chemischen Gesellschaft (1882), volume 15, p. 1635–1639 (in German).</ref>
Barfoed testEdit
In Barfoed's test,<ref name="barfoed">Template:Cite journal</ref> a solution of dissolved copper acetate, sodium acetate and acetic acid is added to the solution of the sugar to be tested and subsequently heated in a water bath for a few minutes. Glucose and other monosaccharides rapidly produce a reddish color and reddish brown copper(I) oxide (Cu2O).
Nylander's testEdit
As a reducing sugar, glucose reacts in the Nylander's test.<ref>Emil Nylander: Über alkalische Wismuthlösung als Reagens auf Traubenzucker im Harne, Zeitschrift für physiologische Chemie. Volume 8, Issue 3, 1884, p. 175–185 Abstract. Template:Webarchive (in German).</ref>
Other testsEdit
Template:See also Upon heating a dilute potassium hydroxide solution with glucose to 100 °C, a strong reddish browning and a caramel-like odor develops.<ref name="Schwedt 102">Georg Schwedt: Zuckersüße Chemie. John Wiley & Sons, 2012, Template:ISBN, p. 102 (in German).</ref> Concentrated sulfuric acid dissolves dry glucose without blackening at room temperature forming sugar sulfuric acid.<ref name="Schwedt 102" />Template:Verify source In a yeast solution, alcoholic fermentation produces carbon dioxide in the ratio of 2.0454 molecules of glucose to one molecule of CO2.<ref name="Schwedt 102" /> Glucose forms a black mass with stannous chloride.<ref name="Schwedt 102" /> In an ammoniacal silver solution, glucose (as well as lactose and dextrin) leads to the deposition of silver. In an ammoniacal lead acetate solution, white lead glycoside is formed in the presence of glucose, which becomes less soluble on cooking and turns brown.<ref name="Schwedt 102" /> In an ammoniacal copper solution, yellow copper oxide hydrate is formed with glucose at room temperature, while red copper oxide is formed during boiling (same with dextrin, except for with an ammoniacal copper acetate solution).<ref name="Schwedt 102" /> With Hager's reagent, glucose forms mercury oxide during boiling.<ref name="Schwedt 102" /> An alkaline bismuth solution is used to precipitate elemental, black-brown bismuth with glucose.<ref name="Schwedt 102" /> Glucose boiled in an ammonium molybdate solution turns the solution blue. A solution with indigo carmine and sodium carbonate destains when boiled with glucose.<ref name="Schwedt 102" />
Instrumental quantificationEdit
Refractometry and polarimetryEdit
In concentrated solutions of glucose with a low proportion of other carbohydrates, its concentration can be determined with a polarimeter. For sugar mixtures, the concentration can be determined with a refractometer, for example in the Oechsle determination in the course of the production of wine.
Photometric enzymatic methods in solutionEdit
{{#invoke:Labelled list hatnote|labelledList|Main article|Main articles|Main page|Main pages}} The enzyme glucose oxidase (GOx) converts glucose into gluconic acid and hydrogen peroxide while consuming oxygen. Another enzyme, peroxidase, catalyzes a chromogenic reaction (Trinder reaction)<ref>Template:Cite journal</ref> of phenol with 4-aminoantipyrine to a purple dye.<ref name="purpuled">Template:Cite book</ref>
Photometric test-strip methodEdit
The test-strip method employs the above-mentioned enzymatic conversion of glucose to gluconic acid to form hydrogen peroxide. The reagents are immobilised on a polymer matrix, the so-called test strip, which assumes a more or less intense color. This can be measured reflectometrically at 510 nm with the aid of an LED-based handheld photometer. This allows routine blood sugar determination by nonscientists. In addition to the reaction of phenol with 4-aminoantipyrine, new chromogenic reactions have been developed that allow photometry at higher wavelengths (550 nm, 750 nm).<ref name="purpuled"/><ref>Template:Cite journal</ref>
Amperometric glucose sensorEdit
The electroanalysis of glucose is also based on the enzymatic reaction mentioned above. The produced hydrogen peroxide can be amperometrically quantified by anodic oxidation at a potential of 600 mV.<ref>Template:Cite journal.</ref> The GOx is immobilized on the electrode surface or in a membrane placed close to the electrode. Precious metals such as platinum or gold are used in electrodes, as well as carbon nanotube electrodes, which e.g. are doped with boron.<ref>Template:Cite journal</ref> Cu–CuO nanowires are also used as enzyme-free amperometric electrodes, reaching a detection limit of 50 μmol/L.<ref>Template:Cite journal</ref> A particularly promising method is the so-called "enzyme wiring", where the electron flowing during the oxidation is transferred via a molecular wire directly from the enzyme to the electrode.<ref>Template:Cite journal</ref>
Other sensory methodsEdit
There are a variety of other chemical sensors for measuring glucose.<ref name="Borisov">Template:Cite journal</ref><ref>Template:Cite journal</ref> Given the importance of glucose analysis in the life sciences, numerous optical probes have also been developed for saccharides based on the use of boronic acids,<ref>Template:Cite journal</ref> which are particularly useful for intracellular sensory applications where other (optical) methods are not or only conditionally usable. In addition to the organic boronic acid derivatives, which often bind highly specifically to the 1,2-diol groups of sugars, there are also other probe concepts classified by functional mechanisms which use selective glucose-binding proteins (e.g. concanavalin A) as a receptor. Furthermore, methods were developed which indirectly detect the glucose concentration via the concentration of metabolized products, e.g. by the consumption of oxygen using fluorescence-optical sensors.<ref>Template:Cite journal</ref> Finally, there are enzyme-based concepts that use the intrinsic absorbance or fluorescence of (fluorescence-labeled) enzymes as reporters.<ref name="Borisov" />
Copper iodometryEdit
Glucose can be quantified by copper iodometry.<ref name="Galant">Template:Cite journal</ref>
Chromatographic methodsEdit
In particular, for the analysis of complex mixtures containing glucose, e.g. in honey, chromatographic methods such as high performance liquid chromatography and gas chromatography<ref name="Galant" /> are often used in combination with mass spectrometry.<ref>Template:Cite journal</ref><ref name="mpg-210190">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Taking into account the isotope ratios, it is also possible to reliably detect honey adulteration by added sugars with these methods.<ref>Template:Cite journal</ref> Derivatization using silylation reagents is commonly used.<ref>Template:Cite journal</ref> Also, the proportions of di- and trisaccharides can be quantified.
In vivo analysisEdit
Glucose uptake in cells of organisms is measured with 2-deoxy-D-glucose or fluorodeoxyglucose.<ref name="Dwyer">Donard Dwyer: Glucose Metabolism in the Brain. Academic Press, 2002, Template:ISBN, p. XIII.</ref> (18F)fluorodeoxyglucose is used as a tracer in positron emission tomography in oncology and neurology,<ref name="gdch">Gesellschaft Deutscher Chemiker: wayback=20100331071121 Anlagen zum Positionspapier der Fachgruppe Nuklearchemie Template:Webarchive, February 2000.</ref> where it is by far the most commonly used diagnostic agent.<ref>Template:Cite journal</ref>
ReferencesEdit
External linksEdit
Template:Diagnostic agents Template:Glycogenesis and glycogenolysis metabolic intermediates Template:Glycolysis Template:Inborn errors of carbohydrate metabolism Template:Carbohydrates Template:Sugar Template:Portal bar Template:Authority control