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Homocitric acid

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Homocitric acid
Names
Preferred IUPAC name 2-Hydroxybutane-1,2,4-tricarboxylic acid
Other names Homocitric acid
Homocitrate
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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)Key: XKJVEVRQMLKSMO-UHFFFAOYSA-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
SMILES
  • O=C(O)CC(O)(C(=O)O)CCC(=O)O
Properties
Chemical formula C7H10O7
Molar mass 206.150 g·mol
Appearance Colorless solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 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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