Structure and Conformation
GABA is found mostly as a zwitterion, that is, with the carboxy group deprotonated and the amino group protonated. Its conformation depends on its environment. In the gas phase, a highly folded conformation is strongly favored because of the electrostatic attraction between the two functional groups. The stabilization is about 50 kcal/mol, according to quantum chemistry calculations. In the solid state, a more 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.
Read more about this topic: gamma-Aminobutyric Acid
Famous quotes containing the words structure and and/or structure:
“One theme links together these new proposals for family policy—the idea that the family is exceedingly durable. Changes in structure and function and individual roles are not to be confused with the collapse of the family. Families remain more important in the lives of children than other institutions. Family ties are stronger and more vital than many of us imagine in the perennial atmosphere of crisis surrounding the subject.”
—Joseph Featherstone (20th century)
“Science is intimately integrated with the whole social structure and cultural tradition. They mutually support one other—only in certain types of society can science flourish, and conversely without a continuous and healthy development and application of science such a society cannot function properly.”
—Talcott Parsons (1902–1979)