aminoadipate

Aminoadipate, commonly referred to as 2-aminoadipic acid, is a six-carbon amino acid with two carboxyl groups and one amino group. Its chemical formula is C6H11NO4. It is a non-proteinogenic amino acid, meaning it is not typically incorporated into proteins in living organisms.

In biology, aminoadipate is most notable as an intermediate in the alpha-aminoadipate pathway, a biosynthetic route used by fungi and some bacteria to produce lysine. In this pathway, aminoadipate derivatives are formed from central metabolic units and are subsequently processed to yield lysine. This pathway is distinct from the lysine biosynthesis route found in plants and bacteria that use the diaminopimelate or standard diaminopropanoate pathways.

Physiochemical properties of aminoadipate include its behavior as a polyvalent acid–base species. At physiological pH, it exists predominantly in an anionic form, with deprotonated carboxyl groups and a protonated amino group, reflecting its amino acid character. Its two carboxyl groups confer acidity, while the amino group provides basic character, contributing to its overall charge and solubility in water. In laboratory settings, aminoadipate and its salts are used as standards or intermediates in metabolic studies and in research on lysine biosynthesis.

Clinical and environmental notes on aminoadipate are limited; it is not a standard dietary amino acid and is not commonly used as a therapeutic agent. It may appear in specialized biochemical research contexts or in studies of lysine metabolism in microorganisms.

See also: lysine biosynthesis, alpha-aminoadipate pathway, 2-aminoadipic acid derivatives.