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Homocitric acid

Names
IUPAC name 2-hydroxybutane-1,2,4-tricarboxylic acid
Other names Homocitric acid Homocitrate
Identifiers
CAS Number	3562-74-1
3D model (JSmol)	Interactive image
PubChem CID	28371
CompTox Dashboard (EPA)	DTXSID10331413
SMILES OC(=O)CCC(O)(CC(O)=O)C(O)=O
Properties
Chemical formula	C7H10O7
Molar mass	206.15 g/mol
Appearance	colorless solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) Infobox references

Homocitric acid is an organic compound with the formula HOC(CO₂H)(CH₂CO₂H)(C₂H₄CO₂H). This tricarboxylic acid occurs naturally as a component of the iron-molybdenum cofactor of certain nitrogenase 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 by the addition of one methylene group, which is implied with the term "homo." Unlike citric acid, homocitric acid is chiral. The acid exists in equilibrium with the lactone.

References

1. Douglas C. Rees "Great Metalloclusters in Enzymology" Annual Reviews of Biochemistry 2002, volume 71, pp. 221–46. doi:10.1146/annurev.biochem.71.110601.135406

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