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Chemical Compound Review

O-acetylserine     3-acetyloxy-2-amino-propanoic acid

Synonyms: AG-A-53438, NSC-16549, NSC-226230, NSC-231949, NSC-408393, ...
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Disease relevance of O-acetyl-L-serine


High impact information on O-acetyl-L-serine


Chemical compound and disease context of O-acetyl-L-serine


Biological context of O-acetyl-L-serine


Anatomical context of O-acetyl-L-serine


Associations of O-acetyl-L-serine with other chemical compounds


Gene context of O-acetyl-L-serine

  • The identity of cys1 was further demonstrated through complementation of an E. coli cysteine auxotroph, which lacks O-acetylserine (thiol) lyase, by expression of the wheat gene [26].
  • NIT3 promoter activity was strongly induced by O-acetylserine, suggesting that, as is the case with enzymes of sulphate assimilation, sulphate deficiency may be communicated to NIT3 via an increase in the level of the cysteine precursor, O-acetylserine [27].
  • The addition of O-acetyl-L-serine to the cysE strain produced a 5.5-fold increase in the rate of synthesis of cys mRNA [28].
  • In vitro transcription runoff studies with DNA template from the S. typhimurium cysJIH promoter region showed synthesis of a product originating at the major in vivo start site, which was dependent on the presence of purified cysB protein and either O-acetyl-L-serine or N-acetyl-L-serine [29].
  • We transformed two commercial strains (UCD522 and UCD713) with a plasmid overexpressing the MET17 gene, which encodes the bifunctional O-acetylserine/O-acetylhomoserine sulfhydrylase (OAS/OAH SHLase), to test the hypothesis that the level of activity of this enzyme limits reduced sulfur incorporation, leading to H(2)S release [30].

Analytical, diagnostic and therapeutic context of O-acetyl-L-serine


  1. Rat cystathionine beta-synthase. Gene organization and alternative splicing. Swaroop, M., Bradley, K., Ohura, T., Tahara, T., Roper, M.D., Rosenberg, L.E., Kraus, J.P. J. Biol. Chem. (1992) [Pubmed]
  2. Role of pyridoxal 5'-phosphate in the structural stabilization of O-acetylserine sulfhydrylase. Bettati, S., Benci, S., Campanini, B., Raboni, S., Chirico, G., Beretta, S., Schnackerz, K.D., Hazlett, T.L., Gratton, E., Mozzarelli, A. J. Biol. Chem. (2000) [Pubmed]
  3. Mechanism of the addition half of the O-acetylserine sulfhydrylase-A reaction. Rabeh, W.M., Alguindigue, S.S., Cook, P.F. Biochemistry (2005) [Pubmed]
  4. Identification of a functional homolog of the Escherichia coli and Salmonella typhimurium cysM gene encoding O-acetylserine sulfhydrylase B in Campylobacter jejuni. Garvis, S.G., Tipton, S.L., Konkel, M.E. Gene (1997) [Pubmed]
  5. O-Acetylserine sulfhydrylase and S-sulfocysteine synthase activities of Rhodospirillum tenue. Hensel, G., Trüper, H.G. Arch. Microbiol. (1983) [Pubmed]
  6. Structure of human cystathionine beta-synthase: a unique pyridoxal 5'-phosphate-dependent heme protein. Meier, M., Janosik, M., Kery, V., Kraus, J.P., Burkhard, P. EMBO J. (2001) [Pubmed]
  7. Dominant-negative modification reveals the regulatory function of the multimeric cysteine synthase protein complex in transgenic tobacco. Wirtz, M., Hell, R. Plant Cell (2007) [Pubmed]
  8. Semisynthetic production of unnatural L-alpha-amino acids by metabolic engineering of the cysteine-biosynthetic pathway. Maier, T.H. Nat. Biotechnol. (2003) [Pubmed]
  9. Thymosins beta 8 and beta 9: two new peptides isolated from calf thymus homologous to thymosin beta 4. Hannappel, E., Davoust, S., Horecker, B.L. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  10. Structure and mechanism of O-acetylserine sulfhydrylase. Rabeh, W.M., Cook, P.F. J. Biol. Chem. (2004) [Pubmed]
  11. Crystallization and preliminary X-ray data for the A-isozyme of O-acetylserine sulfhydrylase from Salmonella typhimurium. Rao, G.S., Mottonen, J., Goldsmith, E.J., Cook, P.F. J. Mol. Biol. (1993) [Pubmed]
  12. Evidence for identity of beta-pyrazolealanine synthase with cysteine synthase in watermelon: formation of beta-pyrazole-alanine by cloned cysteine synthase in vitro and in vivo. Noji, M., Murakoshi, I., Saito, K. Biochem. Biophys. Res. Commun. (1993) [Pubmed]
  13. Two enzymes together capable of cysteine biosynthesis are encoded on a cyanobacterial plasmid. Nicholson, M.L., Gaasenbeek, M., Laudenbach, D.E. Mol. Gen. Genet. (1995) [Pubmed]
  14. Purification and characterization of O-Acetylserine sulfhydrylase of Corynebacterium glutamicum. Wada, M., Awano, N., Yamazawa, H., Takagi, H., Nakamori, S. Biosci. Biotechnol. Biochem. (2004) [Pubmed]
  15. Use of biomolecular interaction analysis to elucidate the regulatory mechanism of the cysteine synthase complex from Arabidopsis thaliana. Berkowitz, O., Wirtz, M., Wolf, A., Kuhlmann, J., Hell, R. J. Biol. Chem. (2002) [Pubmed]
  16. The molecular basis for positive regulation of cys promoters in Salmonella typhimurium and Escherichia coli. Kredich, N.M. Mol. Microbiol. (1992) [Pubmed]
  17. Phylogeny of metabolic pathways: O-acetylserine sulphydrylase A is homologous to the tryptophan synthase beta subunit. Levy, S., Danchin, A. Mol. Microbiol. (1988) [Pubmed]
  18. Cysteine synthase from Capsicum annuum chromoplasts. Characterization and cDNA cloning of an up-regulated enzyme during fruit development. Römer, S., d'Harlingue, A., Camara, B., Schantz, R., Kuntz, M. J. Biol. Chem. (1992) [Pubmed]
  19. Cloning of the E. coli O-acetylserine sulfhydrylase gene: ability of the clone to produce a mutagenic product from azide and O-acetylserine. Owais, W.M., Gharaibeh, R. Mutat. Res. (1990) [Pubmed]
  20. Catalytic competence of O-acetylserine sulfhydrylase in the crystal probed by polarized absorption microspectrophotometry. Mozzarelli, A., Bettati, S., Pucci, A.M., Burkhard, P., Cook, P.F. J. Mol. Biol. (1998) [Pubmed]
  21. Ligand binding induces a large conformational change in O-acetylserine sulfhydrylase from Salmonella typhimurium. Burkhard, P., Tai, C.H., Ristroph, C.M., Cook, P.F., Jansonius, J.N. J. Mol. Biol. (1999) [Pubmed]
  22. Regulation of expression of a cDNA from barley roots encoding a high affinity sulphate transporter. Smith, F.W., Hawkesford, M.J., Ealing, P.M., Clarkson, D.T., Vanden Berg, P.J., Belcher, A.R., Warrilow, A.G. Plant J. (1997) [Pubmed]
  23. Three-dimensional structure of O-acetylserine sulfhydrylase from Salmonella typhimurium. Burkhard, P., Rao, G.S., Hohenester, E., Schnackerz, K.D., Cook, P.F., Jansonius, J.N. J. Mol. Biol. (1998) [Pubmed]
  24. Random-order ternary complex reaction mechanism of serine acetyltransferase from Escherichia coli. Hindson, V.J., Shaw, W.V. Biochemistry (2003) [Pubmed]
  25. Structural insights into catalysis and inhibition of O-acetylserine sulfhydrylase from Mycobacterium tuberculosis. Crystal structures of the enzyme alpha-aminoacrylate intermediate and an enzyme-inhibitor complex. Schnell, R., Oehlmann, W., Singh, M., Schneider, G. J. Biol. Chem. (2007) [Pubmed]
  26. Tobacco plants transformed with the O-acetylserine (thiol) lyase gene of wheat are resistant to toxic levels of hydrogen sulphide gas. Youssefian, S., Nakamura, M., Sano, H. Plant J. (1993) [Pubmed]
  27. A role for nitrilase 3 in the regulation of root morphology in sulphur-starving Arabidopsis thaliana. Kutz, A., Müller, A., Hennig, P., Kaiser, W.M., Piotrowski, M., Weiler, E.W. Plant J. (2002) [Pubmed]
  28. Isolation of a lambdadcys transducing bacteriophage and its use in determining the regulation of cysteine messenger ribonucleic acid synthesis in Escherichia coli K-12. Fimmel, A.L., Loughlin, R.E. J. Bacteriol. (1977) [Pubmed]
  29. Molecular characterization of the cysJIH promoters of Salmonella typhimurium and Escherichia coli: regulation by cysB protein and N-acetyl-L-serine. Ostrowski, J., Kredich, N.M. J. Bacteriol. (1989) [Pubmed]
  30. MET17 and hydrogen sulfide formation in Saccharomyces cerevisiae. Spiropoulos, A., Bisson, L.F. Appl. Environ. Microbiol. (2000) [Pubmed]
  31. The cysP promoter of Salmonella typhimurium: characterization of two binding sites for CysB protein, studies of in vivo transcription initiation, and demonstration of the anti-inducer effects of thiosulfate. Hryniewicz, M.M., Kredich, N.M. J. Bacteriol. (1991) [Pubmed]
  32. Molecular genetics of met 17 and met 25 mutants of Saccharomyces cerevisiae: intragenic complementation between mutations of a single structural gene. D'Andrea, R., Surdin-Kerjan, Y., Pure, G., Cherest, H. Mol. Gen. Genet. (1987) [Pubmed]
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