Open main menu
Home
Random
Recent changes
Special pages
Community portal
Preferences
About Wikipedia
Disclaimers
Incubator escapee wiki
Search
User menu
Talk
Dark mode
Contributions
Create account
Log in
Editing
GABA
(section)
Warning:
You are not logged in. Your IP address will be publicly visible if you make any edits. If you
log in
or
create an account
, your edits will be attributed to your username, along with other benefits.
Anti-spam check. Do
not
fill this in!
== Structure and conformation == GABA is found mostly as a [[zwitterion]] (i.e., with the [[carboxyl]] group deprotonated and the amino group protonated). Its [[conformational isomerism|conformation]] depends on its environment. In the gas phase, a highly folded conformation is strongly favored due to the electrostatic attraction between the two functional groups. The stabilization is about 50 kcal/mol, according to [[quantum chemistry]] calculations. In the solid state, an extended conformation is found, with a trans conformation at the amino end and a gauche conformation at the carboxyl end. This is due to the packing interactions with the neighboring molecules. In solution, five different conformations, some folded and some extended, are found as a result of [[solvation]] effects. The conformational flexibility of GABA is important for its biological function, as it has been found to bind to different receptors with different conformations. Many GABA analogues with pharmaceutical applications have more rigid structures in order to control the binding better.<ref name="Majumdar Guha 1988">{{cite journal |vauthors= Majumdar D, Guha S |year= 1988 |title= Conformation, electrostatic potential and pharmacophoric pattern of GABA (γ-aminobutyric acid) and several GABA inhibitors |journal= Journal of Molecular Structure: THEOCHEM |volume= 180 |pages= 125–140 |doi= 10.1016/0166-1280(88)80084-8}}</ref><ref>{{cite book |vauthors= Sapse AM |title=Molecular Orbital Calculations for Amino Acids and Peptides |publisher= Birkhäuser |year= 2000 |isbn= 978-0-8176-3893-1}}{{page needed|date=May 2013}}</ref>
Edit summary
(Briefly describe your changes)
By publishing changes, you agree to the
Terms of Use
, and you irrevocably agree to release your contribution under the
CC BY-SA 4.0 License
and the
GFDL
. You agree that a hyperlink or URL is sufficient attribution under the Creative Commons license.
Cancel
Editing help
(opens in new window)