Editing Pyridoxal phosphate (section)

{{short description|Active form of vitamin B6}}
{{cs1 config|name-list-style=vanc}}
{{chembox
| Verifiedfields = changed
| verifiedrevid = 393759663
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Pyridoxal-phosphate.svg
| ImageSize =
| ImageName = Skeletal formula
| ImageClass= skin-invert-image
| ImageCaption = Idealised [[skeletal formula]]
| ImageFile1 = Pyridoxal-phosphate-from-xtal-3D-bs-17.png
| ImageSize1 = 210px
| ImageName1 = Ball-and-stick model
| ImageCaption1 = [[Ball-and-stick model]] based on the [[crystal structure]].<ref name="PLPHYD10">{{cite journal | url = https://www.ccdc.cam.ac.uk/structures/Search?Ccdcid=1235193&DatabaseToSearch=Published | title = CSD Entry: PLPHYD10 | website = [[Cambridge Structural Database]]: Access Structures | year = 1974 | publisher = [[Cambridge Crystallographic Data Centre]] | access-date = 2023-11-04 | archive-date = 2023-11-04 | archive-url = https://web.archive.org/web/20231104212545/https://www.ccdc.cam.ac.uk/structures/Search?Ccdcid=1235193&DatabaseToSearch=Published | url-status = live }}</ref><ref>{{ cite journal | first1 = T. | last1 = Fujiwara | title = The Crystal and Molecular Structure of Vitamin B<sub>6</sub> Derivatives. I. Pyridoxal Phosphate Hydrate and Pyridoxal Phosphate Methyl Hemiacetal | journal = [[Bulletin of the Chemical Society of Japan|Bull. Chem. Soc. Jpn.]] | year = 1973 | volume = 46 | issue = 3 | pages = 863–871 | doi = 10.1246/bcsj.46.863 | doi-access = free }}</ref> Note that the phosphate and [[pyridine]] groups have reacted to form a [[zwitterion]] and the [[aldehyde]] group is [[Geminal diol|hydrated]].
| PIN =(4-Formyl-5-hydroxy-6-methylpyridin-3-yl)methyl dihydrogen phosphate
| OtherNames = Pyridoxal 5-phosphate, PAL-P, PLP, Vitamin B6 phosphate
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 5249
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo =54-47-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = F06SGE49M6
| PubChem =1051
| ChEBI = 18405
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 82202
| SMILES = O=Cc1c(O)c(C)ncc1COP(O)(O)=O
| MeSHName =Pyridoxal+Phosphate
  }}
|Section2={{Chembox Properties
| Formula =C<sub>8</sub>H<sub>10</sub>NO<sub>6</sub>P
| MolarMass =247.142 g/mol
| Appearance =
| Density =1.638±0.06 g/cm3<ref name="ReferenceA">Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2011 ACD/Labs)</ref>
| MeltingPtC = 139 to 142
| MeltingPt_ref = <ref>{{cite journal | vauthors = Kozlov ÉI, L'vova MS | title = Stability of water-soluble vitamins and coenzymes. Hydrolysis of pyridoxal-5-phosphate in acidic, neutral, and weakly alkaline solutions. | journal = Pharmaceutical Chemistry Journal | date = 1978 | volume = 11 | issue = 11 | pages = 1543–9 | doi = 10.1007/BF00778244 | s2cid = 1094223 }}</ref>
| BoilingPt =
| Solubility =
| pKa =1.56<ref name="ReferenceA"/>
  }}
|Section6={{Chembox Pharmacology
| ATCCode_prefix = A11
| ATCCode_suffix = HA06
}}
|Section7={{Chembox Hazards
| MainHazards =
| FlashPt =296.0±32.9 °C<ref name="ReferenceA"/>
| AutoignitionPt =
 }}
}}

'''Pyridoxal phosphate''' ('''PLP''', [[pyridoxal]] 5'-[[phosphate]], '''P5P'''), the active form of [[vitamin B6|vitamin B<sub>6</sub>]], is a [[coenzyme]] in a variety of [[enzymatic]] reactions. The [[International Union of Biochemistry and Molecular Biology]] has catalogued more than 140 PLP-dependent activities, corresponding to ~4% of all classified activities.<ref>{{cite journal | vauthors = Percudani R, Peracchi A | title = A genomic overview of pyridoxal-phosphate-dependent enzymes | journal = EMBO Reports | volume = 4 | issue = 9 | pages = 850–4 | date = September 2003 | pmid = 12949584 | pmc = 1326353 | doi = 10.1038/sj.embor.embor914 }}</ref> The versatility of PLP arises from its ability to covalently bind the substrate, and then to act as an electrophilic catalyst, thereby stabilizing different types of carbanionic reaction intermediates.