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