Literature DB >> 475760

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

J O'Sullivan, R T Aplin, C M Stevens, E P Abraham.   

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.

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Year:  1979        PMID： 475760      PMCID： PMC1186593          DOI： 10.1042/bj1790047

Source DB:  PubMed          Journal:  Biochem J        ISSN： 0264-6021            Impact factor:   3.857


  10 in total

1.  Colorimetric detection of penicillins and cephalosporins on paper.

Authors:  R THOMAS
Journal:  Nature       Date:  1961-09-16       Impact factor: 49.962

2.  Nocardicin A, a new monocyclic beta-lactam antibiotic. I. Discovery, isolation and characterization.

Authors:  H Aoki; H Sakai; M Kohsaka; T Konomi; J Hosoda
Journal:  J Antibiot (Tokyo)       Date:  1976-05       Impact factor: 2.649

3.  Naturally-occurring beta-lactamase inhibitors with antibacterial activity.

Authors:  A G Brown; D Butterworth; M Cole; G Hanscomb; J D Hood; C Reading; G N Rolinson
Journal:  J Antibiot (Tokyo)       Date:  1976-06       Impact factor: 2.649

4.  Letter: The occurrence of deacetoxycephalosporin C in fungi and streptomycetes.

Authors:  C E Higgens; R L Hamill; T H Sands; M M Hoehn; N E Davis
Journal:  J Antibiot (Tokyo)       Date:  1974-04       Impact factor: 2.649

5.  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].

Authors:  S J Brewer; J E Farthing; M K Turner
Journal:  Biochem Soc Trans       Date:  1977       Impact factor: 5.407

6.  Beta-lactam antibiotics from Streptomyces.

Authors:  R Nagarajan; L D Boeck; M Gorman; R L Hamill; C E Higgens; M M Hoehn; W M Stark; J G Whitney
Journal:  J Am Chem Soc       Date:  1971-05-05       Impact factor: 15.419

7.  Synthesis of delta-(alpha-aminoadipyl)cysteinylvaline and its role in penicillin biosynthesis.

Authors:  P A Fawcett; J J Usher; J A Huddleston; R C Bleaney; J J Nisbet; E P Abraham
Journal:  Biochem J       Date:  1976-09-01       Impact factor: 3.857

8.  Biosynthesis of penicillin N and cephalosporin C. Antibiotic production and other features of the metabolism of Cephalosporium sp.

Authors:  B Smith; S C Warren; G G Newton; E P Abraham
Journal:  Biochem J       Date:  1967-06       Impact factor: 3.857

9.  Chemical-ionization mass spectrometry of beta-lactam antibiotics.

Authors:  L A Mitscher; H D Showalter; K Shirahata; R L Foltz
Journal:  J Antibiot (Tokyo)       Date:  1975-09       Impact factor: 2.649

10.  Incorporation of labeled precursors into A16886B, a novel -lactam antibiotic produced by Streptomyces clavuligerus.

Authors:  J G Whitney; D R Brannon; J A Mabe; K J Wicker
Journal:  Antimicrob Agents Chemother       Date:  1972-03       Impact factor: 5.191
  10 in total
  9 in total

1.  Production of clavulanic acid and cephamycin C by Streptomyces clavuligerus in palm-oil medium.

Authors:  P C Lee; C C Ho
Journal:  World J Microbiol Biotechnol       Date:  1996-01       Impact factor: 3.312

2.  Induction of holomycin production and complex metabolic changes by the argR mutation in Streptomyces clavuligerus NP1.

Authors:  Hua Yin; Sihai Xiang; Jianting Zheng; Keqiang Fan; Tingting Yu; Xu Yang; Yanfeng Peng; Haibin Wang; Deqin Feng; Yuanming Luo; Hua Bai; Keqian Yang
Journal:  Appl Environ Microbiol       Date:  2012-02-17       Impact factor: 4.792

3.  A two-protein component 7 alpha-cephem-methoxylase encoded by two genes of the cephamycin C cluster converts cephalosporin C to 7-methoxycephalosporin C.

Authors:  J J Coque; F J Enguita; J F Martín; P Liras
Journal:  J Bacteriol       Date:  1995-04       Impact factor: 3.490

4.  Purification of isopenicillin N synthetase.

Authors:  C P Pang; B Chakravarti; R M Adlington; H H Ting; R L White; G S Jayatilake; J E Baldwin; E P Abraham
Journal:  Biochem J       Date:  1984-09-15       Impact factor: 3.857

5.  pcd mutants of Streptomyces clavuligerus still produce cephamycin C.

Authors:  Dylan C Alexander; Cecilia L Anders; Linda Lee; Susan E Jensen
Journal:  J Bacteriol       Date:  2007-06-15       Impact factor: 3.490

6.  The conversion of cephalosporins to 7 alpha-methoxycephalosporins by cell-free extracts of Streptomyces clavuligerus.

Authors:  J O'Sullivan; E P Abraham
Journal:  Biochem J       Date:  1980-02-15       Impact factor: 3.857

7.  Biosynthesis of monobactam compounds: origin of the carbon atoms in the beta-lactam ring.

Authors:  J O'Sullivan; A M Gillum; C A Aklonis; M L Souser; R B Sykes
Journal:  Antimicrob Agents Chemother       Date:  1982-04       Impact factor: 5.191

Review 8.  Genes for beta-lactam antibiotic biosynthesis.

Authors:  J F Martín; S Gutiérrez
Journal:  Antonie Van Leeuwenhoek       Date:  1995       Impact factor: 2.271

Review 9.  Roles of 2-oxoglutarate oxygenases and isopenicillin N synthase in β-lactam biosynthesis.

Authors:  Patrick Rabe; Jos J A G Kamps; Christopher J Schofield; Christopher T Lohans
Journal:  Nat Prod Rep       Date:  2018-08-15       Impact factor: 13.423
  9 in total

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