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Chemical Compound Review

Homocitrate     (2R)-2-hydroxybutane-1,2,4- tricarboxylic acid

Synonyms: AG-F-23535, CHEBI:52222, HMDB03518, CTK0C1235, AC1L97E5, ...
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Disease relevance of Homocitrate


High impact information on Homocitrate


Chemical compound and disease context of Homocitrate


Biological context of Homocitrate

  • With appropriate homocitrate analogues, aberrant forms of FeMo-co are synthesized that exhibit altered substrate specificity and inhibitor susceptibility [12].
  • Fluorohomocitrate does not inhibit the uptake of homocitrate because the wild-type phenotype resulted when both compounds were added to the medium during nitrogenase derepression [9].
  • A 2071-bp DNA fragment, containing a gene (lys1) encoding a protein that showed 71.1% identical amino acids with the Yarrowia lipolytica homocitrate synthase and 71.7% identity with the Saccharomyces cerevisiae homologous enzyme, was cloned from a genomic library of Penicillium chrysogenum [13].
  • In Saccharomyces cerevisae, feedback inhibition of homocitrate synthase isoenzymes by lysine modulates the activation of LYS gene expression by Lys14p [14].
  • Some of these transformants, particularly Ti-C4 (integrative) and TAR-L9 (with autonomously replicating plasmids) showed very high levels of lys1 transcript and, in the case of TAR-L9, high levels of homocitrate synthase activity in cultures of 120 h [15].

Associations of Homocitrate with other chemical compounds


Gene context of Homocitrate

  • Lysine overproduction by one of the mutants seemed to be due to, at least, the loss of repression of the homocitrate synthase encoded by the LYS20 gene [21].
  • In this report we demonstrate that Saccharomyces cerevisiae possesses two genes, LYS20 and LYS21, encoding two homocitrate synthase isoenzymes which are located in the nucleus [14].
  • In spite of extensive genetic analysis, no mutation affecting this step has been isolated until now in model organisms such as Saccharomyces cerevisiae or Neurospora crassa, although identification of mutations affecting the structural gene (LYS1) for homocitrate synthase was reported in the yeast Yarrowia lipolytica several years ago [22].
  • Urinary excretion of homocitric acid and methylhomocitric acid in propionic acidaemia: minor metabolic products of the citrate synthase aldol condensation reaction [23].

Analytical, diagnostic and therapeutic context of Homocitrate


  1. Citrate substitutes for homocitrate in nitrogenase of a nifV mutant of Klebsiella pneumoniae. Liang, J., Madden, M., Shah, V.K., Burris, R.H. Biochemistry (1990) [Pubmed]
  2. Purification of the Azotobacter vinelandii nifV-encoded homocitrate synthase. Zheng, L., White, R.H., Dean, D.R. J. Bacteriol. (1997) [Pubmed]
  3. Identification and characterization of the nifV-nifZ-nifT gene region from the filamentous cyanobacterium Anabaena sp. strain PCC 7120. Stricker, O., Masepohl, B., Klipp, W., Böhme, H. J. Bacteriol. (1997) [Pubmed]
  4. Nucleotide sequence and genetic analysis of the Rhodobacter capsulatus ORF6-nifUI SVW gene region: possible role of NifW in homocitrate processing. Masepohl, B., Angermüller, S., Hennecke, S., Hübner, P., Moreno-Vivian, C., Klipp, W. Mol. Gen. Genet. (1993) [Pubmed]
  5. From the Cover: Nitrogen Fixation Special Feature: Nitrogenase Fe protein: A molybdate/homocitrate insertase. Hu, Y., Corbett, M.C., Fay, A.W., Webber, J.A., Hodgson, K.O., Hedman, B., Ribbe, M.W. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  6. Inactivation of homocitrate synthase causes lysine auxotrophy in copper/zinc-containing superoxide dismutase-deficient yeast Schizosaccharomyces pombe. Kwon, E.S., Jeong, J.H., Roe, J.H. J. Biol. Chem. (2006) [Pubmed]
  7. Regulatory mechanism of histidine-tagged homocitrate synthase from Saccharomyces cerevisiae. II. Theory. Andi, B., Cook, P.F. J. Biol. Chem. (2005) [Pubmed]
  8. Homocitrate synthase is located in the nucleus in the yeast Saccharomyces cerevisiae. Chen, S., Brockenbrough, J.S., Dove, J.E., Aris, J.P. J. Biol. Chem. (1997) [Pubmed]
  9. Effects of homocitrate, homocitrate lactone, and fluorohomocitrate on nitrogenase in NifV- mutants of Azotobacter vinelandii. Madden, M.S., Paustian, T.D., Ludden, P.W., Shah, V.K. J. Bacteriol. (1991) [Pubmed]
  10. New open reading frames, one of which is similar to the nifV gene of Azotobacter vinelandii, found on a 12.5 kbp fragment of chromosome IV of Saccharomyces cerevisiae. Verhasselt, P., Voet, M., Volckaert, G. Yeast (1995) [Pubmed]
  11. Kinetics and product analysis of the reaction catalysed by recombinant homoaconitase from Thermus thermophilus. Jia, Y., Tomita, T., Yamauchi, K., Nishiyama, M., Palmer, D.R. Biochem. J. (2006) [Pubmed]
  12. Dinitrogenase with altered substrate specificity results from the use of homocitrate analogues for in vitro synthesis of the iron-molybdenum cofactor. Hoover, T.R., Imperial, J., Liang, J.H., Ludden, P.W., Shah, V.K. Biochemistry (1988) [Pubmed]
  13. Characterization and lysine control of expression of the lys1 gene of Penicillium chrysogenum encoding homocitrate synthase. Bañuelos, O., Casqueiro, J., Fierro, F., Hijarrubia, M.J., Gutiérrez, S., Martín, J.F. Gene (1999) [Pubmed]
  14. In Saccharomyces cerevisae, feedback inhibition of homocitrate synthase isoenzymes by lysine modulates the activation of LYS gene expression by Lys14p. Feller, A., Ramos, F., Piérard, A., Dubois, E. Eur. J. Biochem. (1999) [Pubmed]
  15. Overexpression of the lys1 gene in Penicillium chrysogenum: homocitrate synthase levels, alpha-aminoadipic acid pool and penicillin production. Bañuelos, O., Casqueiro, J., Gutiérrez, S., Martín, J.F. Appl. Microbiol. Biotechnol. (2000) [Pubmed]
  16. In vitro synthesis of the iron-molybdenum cofactor of nitrogenase. Purification and characterization of NifB cofactor, the product of NIFB protein. Shah, V.K., Allen, J.R., Spangler, N.J., Ludden, P.W. J. Biol. Chem. (1994) [Pubmed]
  17. Substrate reduction properties of dinitrogenase activated in vitro are dependent upon the presence of homocitrate or its analogues during iron-molybdenum cofactor synthesis. Imperial, J., Hoover, T.R., Madden, M.S., Ludden, P.W., Shah, V.K. Biochemistry (1989) [Pubmed]
  18. Acid-Base Chemical Mechanism of Homocitrate Synthase from Saccharomyces cerevisiae. Qian, J., West, A.H., Cook, P.F. Biochemistry (2006) [Pubmed]
  19. Nucleotide sequence and genetic analysis of the Azotobacter chroococcum nifUSVWZM gene cluster, including a new gene (nifP) which encodes a serine acetyltransferase. Evans, D.J., Jones, R., Woodley, P.R., Wilborn, J.R., Robson, R.L. J. Bacteriol. (1991) [Pubmed]
  20. Stabilization and characterization of histidine-tagged homocitrate synthase from Saccharomyces cerevisiae. Andi, B., West, A.H., Cook, P.F. Arch. Biochem. Biophys. (2004) [Pubmed]
  21. Lysine-overproducing mutants of Saccharomyces cerevisiae baker's yeast isolated in continuous culture. Gasent-Ramírez, J.M., Benítez, T. Appl. Environ. Microbiol. (1997) [Pubmed]
  22. Cloning and sequencing of the LYS1 gene encoding homocitrate synthase in the yeast Yarrowia lipolytica. Perez-Campo, F.M., Nicaud, J.M., Gaillardin, C., Dominguez, A. Yeast (1996) [Pubmed]
  23. Urinary excretion of homocitric acid and methylhomocitric acid in propionic acidaemia: minor metabolic products of the citrate synthase aldol condensation reaction. van Rooyen, J.P., Mienie, L.J., Erasmus, E., de Wet, W.J., Duran, M., Wadman, S.K. Clin. Chim. Acta (1994) [Pubmed]
  24. Homocitrate synthase from Penicillium chrysogenum. Localization, purification of the cytosolic isoenzyme, and sensitivity to lysine. Jaklitsch, W.M., Kubicek, C.P. Biochem. J. (1990) [Pubmed]
  25. The Aspergillus nidulans lysF gene encodes homoaconitase, an enzyme involved in the fungus-specific lysine biosynthesis pathway. Weidner, G., Steffan, B., Brakhage, A.A. Mol. Gen. Genet. (1997) [Pubmed]
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