Skip to main content
Biochemical Journal logoLink to Biochemical Journal
. 1979 Apr 1;179(1):47–52. doi: 10.1042/bj1790047

Biosynthesis of a 7-alpha-methoxycephalosporin. Incorporation of molecular oxygen.

J O'Sullivan, R T Aplin, C M Stevens, E P Abraham
PMCID: PMC1186593  PMID: 475760

Abstract

A 7-alpha-methoxycephalosporin containing a carbamoyloxymethyl substituent at C-3 (cephamycin C) has been isolated from the extracellular fluid of an aqueous suspension of Streptomyces clavuligerus shaken in the presence of 18O2. The cephalosporin has been converted into its N-acetyl dimethyl ester and the distribution of 18O in the latter determined by chemical-ionization mass spectrometry. The results indicate that the oxygen atom of the methoxy group, as well as that linked to the exocyclic methylene group at C-3, is derived from molecular O2.

Full text

PDF
47

Selected References

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

  1. Aoki H., Sakai H., Kohsaka M., Konomi T., Hosoda J. Nocardicin A, a new monocyclic beta-lactam antibiotic. I. Discovery, isolation and characterization. J Antibiot (Tokyo) 1976 May;29(5):492–500. doi: 10.7164/antibiotics.29.492. [DOI] [PubMed] [Google Scholar]
  2. Brewer S. J., Farthing J. E., Turner M. K. The oxygenation of the 3-methyl group of 7beta-(5-D-aminoadipamido)-3-methylceph-3-em-4-carboxylic acid (desacetoxycephalosporin C) by extracts of Acremonium chrysogenum [proceedings]. Biochem Soc Trans. 1977;5(4):1024–1026. doi: 10.1042/bst0051024. [DOI] [PubMed] [Google Scholar]
  3. Brown A. G., Butterworth D., Cole M., Hanscomb G., Hood J. D., Reading C., Rolinson G. N. Naturally-occurring beta-lactamase inhibitors with antibacterial activity. J Antibiot (Tokyo) 1976 Jun;29(6):668–669. doi: 10.7164/antibiotics.29.668. [DOI] [PubMed] [Google Scholar]
  4. Fawcett P. A., Usher J. J., Huddleston J. A., Bleaney R. C., Nisbet J. J., Abraham E. P. Synthesis of delta-(alpha-aminoadipyl)cysteinylvaline and its role in penicillin biosynthesis. Biochem J. 1976 Sep 1;157(3):651–660. doi: 10.1042/bj1570651. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Higgens C. E., Hamill R. L., Sands T. H., Hoehn M. M., Davis N. E. Letter: The occurrence of deacetoxycephalosporin C in fungi and streptomycetes. J Antibiot (Tokyo) 1974 Apr;27(4):298–300. doi: 10.7164/antibiotics.27.298. [DOI] [PubMed] [Google Scholar]
  6. Mitscher L. A., Showalter H. D., Shirahata K., Foltz R. L. Chemical-ionization mass spectrometry of beta-lactam antibiotics. J Antibiot (Tokyo) 1975 Sep;28(9):668–675. doi: 10.7164/antibiotics.28.668. [DOI] [PubMed] [Google Scholar]
  7. Nagarajan R., Boeck L. D., Gorman M., Hamill R. L., Higgens C. E., Hoehn M. M., Stark W. M., Whitney J. G. Beta-lactam antibiotics from Streptomyces. J Am Chem Soc. 1971 May 5;93(9):2308–2310. doi: 10.1021/ja00738a035. [DOI] [PubMed] [Google Scholar]
  8. Smith B., Warren S. C., Newton G. G., Abraham E. P. Biosynthesis of penicillin N and cephalosporin C. Antibiotic production and other features of the metabolism of Cephalosporium sp. Biochem J. 1967 Jun;103(3):877–890. doi: 10.1042/bj1030877. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. THOMAS R. Colorimetric detection of penicillins and cephalosporins on paper. Nature. 1961 Sep 16;191:1161–1163. doi: 10.1038/1911161a0. [DOI] [PubMed] [Google Scholar]
  10. Whitney J. G., Brannon D. R., Mabe J. A., Wicker K. J. Incorporation of labeled precursors into A16886B, a novel -lactam antibiotic produced by Streptomyces clavuligerus. Antimicrob Agents Chemother. 1972 Mar;1(3):247–251. doi: 10.1128/aac.1.3.247. [DOI] [PMC free article] [PubMed] [Google Scholar]

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

RESOURCES