Skip to main content
PMC home page
Biochemical Journal logoLink to Biochemical Journal
. 1975 May;147(2):283–289. doi: 10.1042/bj1470283

Acetylation of S-substituted cysteines by a rat liver and kidney microsomal N-acetyltransferase.

R M Green, J S Elce
PMCID: PMC1165442  PMID: 241322

Abstract

1. An acetyl-CoA--S-substituted cysteine N-acetyltransferase in rat liver and kidney preparations was investigated, by using an assay involving incubations with S-benzyl-L-cysteine and [l-14C]acetyl-CoA and extraction of the radioactive product with ethyl acetate. 2. The enzyme was associated with the microsomal fraction and could not be solubilized. Metal ions, EDTA and detergents did not significantly affect the enzyme activity. p-Chloromercuribenzoate and N-ethylmaleimide inhibited the enzyme. 3. Other S-substituted cysteines were acetylated at about the same rate as S-benzyl-L-cysteine. Acetylation of cysteine itself and of methionine, ethionine and tryptophan could be detected but was much slower. Acetylation of aspartic acid, glycine, phenylalanine and serine could not be detected. Palmitoyl-CoA was not a substrate. 4. The enzyme is presumably responsible for the acetylation step of mercapturic acid synthesis; a more physiological function is not yet known, except that the enzyme may be involved in acetylation of those amino acids which occur in elevated amounts in some disorders of amino acid metabolism.

Full text

PDF

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Auditore J. V., Wade L. H. N-acetyl-L-asparagine in human brain. Neuropharmacology. 1972 May;11(3):385–394. doi: 10.1016/0028-3908(72)90024-x. [DOI] [PubMed] [Google Scholar]
  2. Auditore J. V., Wade L. Occurrence of N-acetylalanine in the human brain. J Neurochem. 1971 Dec;18(12):2389–2395. doi: 10.1111/j.1471-4159.1971.tb00194.x. [DOI] [PubMed] [Google Scholar]
  3. BRAY H. G., JAMES S. P., THORPE W. V. Metabolism of o-, m- and p-fluoro-, bromo- and -iodo-nitrobenzenes in the rabbit. Biochem J. 1958 Apr;68(4):561–568. doi: 10.1042/bj0680561b. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Barnsley E. A., Eskin N. A., James S. P., Waring R. H. The acetylation of S-alkylcysteines by the rat. Biochem Pharmacol. 1969 Oct;18(10):2393–2401. doi: 10.1016/0006-2952(69)90354-2. [DOI] [PubMed] [Google Scholar]
  5. Berlinguet L., Laliberté M. Biosynthesis of N-acetyl-L-aspartic acid in vivo and in brain homogenates. Can J Biochem. 1970 Feb;48(2):207–211. doi: 10.1139/o70-034. [DOI] [PubMed] [Google Scholar]
  6. Brown B. J., Jellinck P. H. Factors affecting the activity of oestradiol hydroxylase in rat liver microsomal subfractions. Biochem J. 1971 Aug;124(1):91–97. doi: 10.1042/bj1240091. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Cinti D. L., Moldeus P., Schenkman J. B. Kinetic parameters of drug-metabolizing enzymes in Ca 2+ -sedimented microsomes from rat liver. Biochem Pharmacol. 1972 Dec 15;21(24):3249–3256. doi: 10.1016/0006-2952(72)90089-5. [DOI] [PubMed] [Google Scholar]
  8. Cleland W. W. The statistical analysis of enzyme kinetic data. Adv Enzymol Relat Areas Mol Biol. 1967;29:1–32. doi: 10.1002/9780470122747.ch1. [DOI] [PubMed] [Google Scholar]
  9. Coleman R. Membrane-bound enzymes and membrane ultrastructure. Biochim Biophys Acta. 1973 Apr 3;300(1):1–30. doi: 10.1016/0304-4157(73)90010-5. [DOI] [PubMed] [Google Scholar]
  10. DAVIDSON E. A., BLUMENTHAL H. J., ROSEMAN S. Glucosamine metabolism. II. Studies on glucosamine 6-phosphate N-acetylase. J Biol Chem. 1957 May;226(1):125–133. [PubMed] [Google Scholar]
  11. DE DUVE C., PRESSMAN B. C., GIANETTO R., WATTIAUX R., APPELMANS F. Tissue fractionation studies. 6. Intracellular distribution patterns of enzymes in rat-liver tissue. Biochem J. 1955 Aug;60(4):604–617. doi: 10.1042/bj0600604. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Elce J. S. Metabolism of a glutathione conjugate of 2-hydroxyoestradiol by rat liver and kidney preparations in vitro. Biochem J. 1970 Mar;116(5):913–917. doi: 10.1042/bj1160913. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Goldstein F. B. The enzymatic synthesis of N-acetyl-L-aspartic acid by subcellular preparations of rat brain. J Biol Chem. 1969 Aug 10;244(15):4257–4260. [PubMed] [Google Scholar]
  14. Hearse D. J., Weber W. W. Multiple N-acetyltransferases and drug metabolism. Tissue distribution, characterization and significance of mammalian N-acetyltransferase. Biochem J. 1973 Mar;132(3):519–526. doi: 10.1042/bj1320519. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. Holtzman J. L., Erickson R. R., Dewan R. K., Bloomfield V. A. Inelastic laser light scattering and particle size of detergent-treated microsomes. Biochem Biophys Res Commun. 1973 May 1;52(1):15–20. doi: 10.1016/0006-291x(73)90947-9. [DOI] [PubMed] [Google Scholar]
  16. Hurst R., Pincock A., Broekhoven L. H. Model discrimination and nonlinear parameter estimation in the analysis of the mechanism of action of beta-hydroxybutyrate dehydrogenase from Rhodopseudomonas spheroides. Biochim Biophys Acta. 1973 Sep 15;321(1):1–26. doi: 10.1016/0005-2744(73)90055-7. [DOI] [PubMed] [Google Scholar]
  17. Kamath S. A., Narayan K. A. Interaction of Ca 2+ with endoplasmic reticulum of rat liver: a standardized procedure for the isolation of rat liver microsomes. Anal Biochem. 1972 Jul;48(1):53–61. doi: 10.1016/0003-2697(72)90169-8. [DOI] [PubMed] [Google Scholar]
  18. Kamath S. A., Rubin E. Interaction of calcium with microsomes: a modified method for the rapid isolation of rat liver microsomes. Biochem Biophys Res Commun. 1972 Oct 6;49(1):52–59. doi: 10.1016/0006-291x(72)90008-3. [DOI] [PubMed] [Google Scholar]
  19. Kodama H., Ikegami T., Araki T. N-monacetylcystine in human urine. Physiol Chem Phys. 1974;6(1):87–89. [PubMed] [Google Scholar]
  20. LANDS W. E., HART P. METABOLISM OF GLYCEROLIPIDS. VI. SPECIFICITIES OF ACYL COENZYME A: PHOSPHOLIPID ACYLTRANSFERASES. J Biol Chem. 1965 May;240:1905–1911. [PubMed] [Google Scholar]
  21. Meister A. On the enzymology of amino acid transport. Science. 1973 Apr 6;180(4081):33–39. doi: 10.1126/science.180.4081.33. [DOI] [PubMed] [Google Scholar]
  22. SEMENZA G. Chromatographic purification of cysteinyl-glycinase. Biochim Biophys Acta. 1957 May;24(2):401–413. doi: 10.1016/0006-3002(57)90212-3. [DOI] [PubMed] [Google Scholar]
  23. Schloot W., Tigges F. J., Blaesner H., Goedde H. W. N-acetyl-transferase and serotonin metabolism in man and other species. I. Hoppe Seylers Z Physiol Chem. 1969 Nov;350(11):1353–1361. doi: 10.1515/bchm2.1969.350.2.1353. [DOI] [PubMed] [Google Scholar]
  24. Seiler N., al-Therib M. J. Acetyl-CoA: 1,4-diaminobutane N-acetyltransferase. Occurrence in vertebrate organs and subcellular localization. Biochim Biophys Acta. 1974 Jul 4;354(2):206–212. doi: 10.1016/0304-4165(74)90007-5. [DOI] [PubMed] [Google Scholar]
  25. Shechter I., Bloch K. Solubilization and purification of trans-farnesyl pyrophosphate-squalene synthetase. J Biol Chem. 1971 Dec 25;246(24):7690–7696. [PubMed] [Google Scholar]
  26. Shigesada K., Tatibana M. Enzymatic synthesis of acetylglutamate by mammalian liver preparations and its stimulation by arginine. Biochem Biophys Res Commun. 1971 Sep;44(5):1117–1124. doi: 10.1016/s0006-291x(71)80201-2. [DOI] [PubMed] [Google Scholar]
  27. Smith R. C. Acetylation of methionine sulfoxide and methionine sulfone by the rat. Biochim Biophys Acta. 1971 Feb 28;261(2):304–309. doi: 10.1016/0304-4165(72)90051-7. [DOI] [PubMed] [Google Scholar]
  28. Smith R. C., Beeman E. A. Excretion of N-acetylethionine sulfoxide by rats treated with ethionine. Biochim Biophys Acta. 1970 May 12;208(2):267–274. doi: 10.1016/0304-4165(70)90245-x. [DOI] [PubMed] [Google Scholar]
  29. Sribney M. Enzymatic synthesis of ceramide. Biochim Biophys Acta. 1966 Dec 7;125(3):542–547. doi: 10.1016/0005-2760(66)90042-7. [DOI] [PubMed] [Google Scholar]
  30. Strandholm J. J., Buist N. R., Kennaway N. G., Curtis H. T. Excretion of -N-acetylcitrulline in citrullinaemia. Biochim Biophys Acta. 1971 Jul 20;244(1):214–216. doi: 10.1016/0304-4165(71)90140-1. [DOI] [PubMed] [Google Scholar]
  31. Suga T., Kumaoka H., Akagi M. Studies on mercapturic acids. Participation of glutathionase in the conversion of glutathione derivatives to cysteine derivatives. J Biochem. 1966 Aug;60(2):133–139. doi: 10.1093/oxfordjournals.jbchem.a128411. [DOI] [PubMed] [Google Scholar]
  32. Weber W. W., Cohen S. N. N-acetylation of drugs: isolation and properties of an N-acetyltransferase from rabbit liver. Mol Pharmacol. 1967 May;3(3):266–273. [PubMed] [Google Scholar]
  33. Weber W. W., Cohen S. N., Steinberg M. S. Purification and properties of N-acetyltransferase from mammalian liver. Ann N Y Acad Sci. 1968 Jul 31;151(2):734–741. doi: 10.1111/j.1749-6632.1968.tb48256.x. [DOI] [PubMed] [Google Scholar]
  34. Yip C. C., Liew C. C. Role of methionine in the initiation of the biosynthesis of bovine proinsulin. Can J Biochem. 1973 Jun;51(6):783–788. doi: 10.1139/o73-097. [DOI] [PubMed] [Google Scholar]

Articles from Biochemical Journal are provided here courtesy of The Biochemical Society

RESOURCES