Skip to main content
NCBI home page
Journal of Bacteriology logoLink to Journal of Bacteriology
. 1994 Mar;176(5):1282–1286. doi: 10.1128/jb.176.5.1282-1286.1994

Cytosylglucuronic acid synthase (cytosine: UDP-glucuronosyltransferase) from Streptomyces griseochromogenes, the first prokaryotic UDP-glucuronosyltransferase.

S J Gould 1, J Guo 1
PMCID: PMC205190  PMID: 8113166

Abstract

Cytosylglucuronic acid synthase (cytosine: UDP-glucuronosyltransferase), the first prokaryotic UDP-GT and a key enzyme in the biosynthesis of the antibiotic blasticidin S, was purified 870-fold. It has optimum activity at a pH of 8.4 to 8.6, Kms of 6.0 (UDP-glucuronic acid) and 243 (cytosine) microM, and a maximum rate of metabolism of 14.6 mumol/min/mg. The apparent M(r) is 43,000. Activity was slightly enhanced by Mg2+ or Ca2+ but was not inhibited by EDTA. Activity was strongly inhibited by UDP. Cytosylglucuronic acid differs from eukaryotic UDP-glucuronosyltransferases in being a soluble protein with no apparent phospholipid requirement.

Full text

PDF
1282

Images in this article

1284Image
on p.1284

Selected References

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

  1. Argoudelis A. D., Baczynskyj L., Kuo M. T., Laborde A. L., Sebek O. K., Truesdell S. E., Shilliday F. B. Arginomycin: production, isolation, characterization and structure. J Antibiot (Tokyo) 1987 Jun;40(6):750–760. doi: 10.7164/antibiotics.40.750. [DOI] [PubMed] [Google Scholar]
  2. Armstrong R. N. Enzyme-catalyzed detoxication reactions: mechanisms and stereochemistry. CRC Crit Rev Biochem. 1987;22(1):39–88. doi: 10.3109/10409238709082547. [DOI] [PubMed] [Google Scholar]
  3. Bock K. W. Roles of UDP-glucuronosyltransferases in chemical carcinogenesis. Crit Rev Biochem Mol Biol. 1991;26(2):129–150. doi: 10.3109/10409239109081125. [DOI] [PubMed] [Google Scholar]
  4. Burchell B., Coughtrie M. W. UDP-glucuronosyltransferases. Pharmacol Ther. 1989;43(2):261–289. doi: 10.1016/0163-7258(89)90122-8. [DOI] [PubMed] [Google Scholar]
  5. Chen T. S., So L., White R., Monaghan R. L. Microbial hydroxylation and glucuronidation of the angiotensin II (AII) receptor antagonist MK 954. J Antibiot (Tokyo) 1993 Jan;46(1):131–134. doi: 10.7164/antibiotics.46.131. [DOI] [PubMed] [Google Scholar]
  6. Cooper R., Conover M., Patel M. Sch 36605, structure of a novel nucleoside. J Antibiot (Tokyo) 1988 Jan;41(1):123–125. doi: 10.7164/antibiotics.41.123. [DOI] [PubMed] [Google Scholar]
  7. Falany C. N., Green M. D., Tephly T. R. The enzymatic mechanism of glucuronidation catalyzed by two purified rat liver steroid UDP-glucuronosyltransferases. J Biol Chem. 1987 Jan 25;262(3):1218–1222. [PubMed] [Google Scholar]
  8. Fox J. J., Watanabe K. A. Nucleosides XXXII. On the Structure of blasticidin S, a nucleoside antibiotic. Tetrahedron Lett. 1966 Mar;9:897–904. doi: 10.1016/s0040-4039(00)76248-4. [DOI] [PubMed] [Google Scholar]
  9. Harada S., Kishi T. Isolation and characterization of mildiomycin, a new nucleoside antibiotic. J Antibiot (Tokyo) 1978 Jun;31(6):519–524. doi: 10.7164/antibiotics.31.519. [DOI] [PubMed] [Google Scholar]
  10. Hirai A., Wildman S. G., Hirai T. Specific inhibition of TMV-RNA synthesis by blasticidin S. Virology. 1968 Dec;36(4):646–651. doi: 10.1016/0042-6822(68)90195-5. [DOI] [PubMed] [Google Scholar]
  11. Hochman Y., Zakim D., Vessey D. A. A kinetic mechanism for modulation of the activity of microsomal UDP-glucuronyltransferase by phospholipids. Effects of lysophosphatidylcholines. J Biol Chem. 1981 May 25;256(10):4783–4788. [PubMed] [Google Scholar]
  12. Larsen S. H., Berry D. M., Paschal J. W., Gilliam J. M. 5-Hydroxymethylblasticidin S and blasticidin S from Streptomyces setonii culture A83094. J Antibiot (Tokyo) 1989 Mar;42(3):470–471. doi: 10.7164/antibiotics.42.470. [DOI] [PubMed] [Google Scholar]
  13. Magdalou J., Hochman Y., Zakim D. Factors modulating the catalytic specificity of a pure form of UDP-glucuronyltransferase. J Biol Chem. 1982 Nov 25;257(22):13624–13629. [PubMed] [Google Scholar]
  14. Matern H., Lappas N., Matern S. Isolation and characterization of hyodeoxycholic-acid: UDP-glucuronosyltransferase from human liver. Eur J Biochem. 1991 Sep 1;200(2):393–400. doi: 10.1111/j.1432-1033.1991.tb16197.x. [DOI] [PubMed] [Google Scholar]
  15. Noort D., Coughtrie M. W., Burchell B., van der Marel G. A., van Boom J. H., van der Gen A., Mulder G. J. Inhibition of UDP-glucuronosyltransferase activity by possible transition-state analogues in rat-liver microsomes. Eur J Biochem. 1990 Mar 10;188(2):309–312. doi: 10.1111/j.1432-1033.1990.tb15404.x. [DOI] [PubMed] [Google Scholar]
  16. SHOMURA T., INOUE M., NIIDA T., HARA T. THE IMPROVED ASSAY METHOD OF BLASTICIDIN S. J Antibiot (Tokyo) 1964 Nov;17:253–261. [PubMed] [Google Scholar]
  17. Sato H., Koiwai O., Tanabe K., Kashiwamata S. Isolation and sequencing of rat liver bilirubin UDP-glucuronosyltransferase cDNA: possible alternate splicing of a common primary transcript. Biochem Biophys Res Commun. 1990 May 31;169(1):260–264. doi: 10.1016/0006-291x(90)91462-2. [DOI] [PubMed] [Google Scholar]
  18. Sedmak J. J., Grossberg S. E. A rapid, sensitive, and versatile assay for protein using Coomassie brilliant blue G250. Anal Biochem. 1977 May 1;79(1-2):544–552. doi: 10.1016/0003-2697(77)90428-6. [DOI] [PubMed] [Google Scholar]
  19. Siest G., Antoine B., Fournel S., Magdalou J., Thomassin J. The glucuronosyltransferases: what progress can pharmacologists expect from molecular biology and cellular enzymology? Biochem Pharmacol. 1987 Apr 1;36(7):983–989. doi: 10.1016/0006-2952(87)90403-5. [DOI] [PubMed] [Google Scholar]
  20. Swaminathan V., Smith J. L., Sundaralingam M., Coutsogeorgopoulos C., Kartha G. Crystal and molecular structure of the antibiotic blasticidin S hydrochloride pentahydrate. Biochim Biophys Acta. 1981 Oct 27;655(3):335–341. doi: 10.1016/0005-2787(81)90043-5. [DOI] [PubMed] [Google Scholar]
  21. TAKEUCHI S., HIRAYAMA K., UEDA K., SAKAI H., YONEHARA H. Blasticidin S, a new antibiotic. J Antibiot (Tokyo) 1958 Jan;11(1):1–5. [PubMed] [Google Scholar]
  22. Takahashi A., Ikeda D., Naganawa H., Okami Y., Umezawa H. Bagougeramines A and B, new nucleoside antibiotics produced by a strain of Bacillus circulans. II. Physico-chemical properties and structure determination. J Antibiot (Tokyo) 1986 Aug;39(8):1041–1046. doi: 10.7164/antibiotics.39.1041. [DOI] [PubMed] [Google Scholar]
  23. Takahashi A., Saito N., Hotta K., Okami Y., Umezawa H. Bagougeramines A and B, new nucleoside antibiotics produced by a strain of Bacillus circulans. I. Taxonomy of the producing organism and isolation and biological properties of the antibiotics. J Antibiot (Tokyo) 1986 Aug;39(8):1033–1040. doi: 10.7164/antibiotics.39.1033. [DOI] [PubMed] [Google Scholar]
  24. Wackett L. P., Gibson D. T. Metabolism of xenobiotic compounds by enzymes in cell extracts of the fungus Cunninghamella elegans. Biochem J. 1982 Jul 1;205(1):117–122. doi: 10.1042/bj2050117. [DOI] [PMC free article] [PubMed] [Google Scholar]
  25. Yonehara H., Otake N. Biological and chemical reconstruction of blasticidin S. Antimicrob Agents Chemother (Bethesda) 1965;5:855–857. [PubMed] [Google Scholar]

Articles from Journal of Bacteriology are provided here courtesy of American Society for Microbiology (ASM)

RESOURCES