Homocitric acid is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula HOC(CO₂H)(CH₂CO₂H)(C₂H₄CO₂H). This

tricarboxylic acid A tricarboxylic acid is an organic carboxylic acid whose chemical structure contains three carboxyl functional groups (-COOH). The best-known example of a tricarboxylic acid is citric acid. Uses Citric acid cycle Citric acid, a type of tricarb ...

occurs naturally as a component of the

iron-molybdenum cofactor FeMoco ( cofactor) is the primary cofactor of nitrogenase. Nitrogenase is the enzyme that catalyzes the conversion of atmospheric nitrogen molecules N2 into ammonia (NH3) through the process known as nitrogen fixation. Containing iron and molybd ...

of certain

nitrogenase Nitrogenases are enzymes () that are produced by certain bacteria, such as cyanobacteria (blue-green bacteria) and rhizobacteria. These enzymes are responsible for the Organic redox reaction, reduction of nitrogen (N2) to ammonia (NH3). Nitrog ...

proteins. Biochemists often refer to this cofactor as homocitrate, which is the conjugate bases that predominate in neutral aqueous solutions of this species. The molecule is related to

citric acid Citric acid is an organic compound with the chemical formula HOC(CO2H)(CH2CO2H)2. It is a colorless weak organic acid. It occurs naturally in citrus fruits. In biochemistry, it is an intermediate in the citric acid cycle, which occurs in t ...

by the addition of one methylene unit, hence the prefix "homo." Unlike citric acid, homocitric acid is

chiral Chirality is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek (''kheir''), "hand", a familiar chiral object. An object or a system is ''chiral'' if it is distinguishable from ...

. The acid exists in equilibrium with the

lactone Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure (), or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Lactones are formed by intramolecular esterification of the co ...

. :

References

Alpha hydroxy acids Chelating agents Tricarboxylic acids {{biochem-stub

See also

References