Homocitric acid

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.[1] Biochemists often refer to this cofactor as homocitrate, which is the conjugate bases that predominate in neutral aqueous solutions of this species.

Homocitric acid
Names
Preferred IUPAC name
2-Hydroxybutane-1,2,4-tricarboxylic acid
Other names
Homocitric acid
Homocitrate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C7H10O7/c8-4(9)1-2-7(14,6(12)13)3-5(10)11/h14H,1-3H2,(H,8,9)(H,10,11)(H,12,13) ☒N
    Key: XKJVEVRQMLKSMO-UHFFFAOYSA-N ☒N
  • InChI=1/C7H10O7/c8-4(9)1-2-7(14,6(12)13)3-5(10)11/h14H,1-3H2,(H,8,9)(H,10,11)(H,12,13)
    Key: XKJVEVRQMLKSMO-UHFFFAOYAL
  • O=C(O)CC(O)(C(=O)O)CCC(=O)O
Properties
C7H10O7
Molar mass 206.150 g·mol−1
Appearance Colorless solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

The molecule is related to citric acid by the addition of one methylene unit, hence the prefix "homo." Unlike citric acid, homocitric acid is chiral. The acid exists in equilibrium with the lactone.

See also

References
  1. Rees, Douglas C. (2002). "Great Metalloclusters in Enzymology" (PDF). Annual Review of Biochemistry. 71: 221–46. doi:10.1146/annurev.biochem.71.110601.135406. PMID 12045096.


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