Literature DB >> 282643

Cell-free ring expansion of penicillin N to deacetoxycephalosporin C by Cephalosporium acremonium CW-19 and its mutants.

M Yoshida, T Konomi, M Kohsaka, J E Baldwin, S Herchen, P Singh, N A Hunt, A L Demain.   

Abstract

To examine microbiological ring expansion of penicillin N to a cephalosporin, we obtained five mutants of Cephalosporium acremonium blocked in beta-lactam antibiotic biosynthesis from 2500 survivors of mutagenesis. In submerged fermentation, mutants M-0198, M-0199, and M-2351 produced no beta-lactam antibiotic (type A), whereas mutants M-1443 and M-1836 formed penicillin N but not cephalosporin C (type B). Cell-free extracts of type A mutants converted penicillin N to a cephalosporin; those of type B mutants did not. The product of the cell-free reaction was identified as deacetoxycephalosporin C by thin-layer chromatography, paper chromatography, paper electrophoresis, and enzyme tests. These data strongly support our hypothesis that penicillin N is an intermediate of cephalosporin biosynthesis.

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Year:  1978        PMID： 282643      PMCID： PMC393159          DOI： 10.1073/pnas.75.12.6253

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  9 in total

1.  Protein measurement with the Folin phenol reagent.

Authors:  O H LOWRY; N J ROSEBROUGH; A L FARR; R J RANDALL
Journal:  J Biol Chem       Date:  1951-11       Impact factor: 5.157

2.  Conversion of penicillin N to cephalosporin(s) by cell-free extracts of Cephalosporium acremonium.

Authors:  M Kohsaka; A L Demain
Journal:  Biochem Biophys Res Commun       Date:  1976-05-17       Impact factor: 3.575

3.  Mutations that affect antibiotic synthesis by Cephalosporium acremonium.

Authors:  P A Lemke; C H Nash
Journal:  Can J Microbiol       Date:  1972-02       Impact factor: 2.419

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.  Studies on the cell-free biosynthesis of beta-lactam antibiotics.

Authors:  P E Bost; A L Demain
Journal:  Biochem J       Date:  1977-03-15       Impact factor: 3.857

6.  Role of methionine in cephalosporin synthesis.

Authors:  P G Caltrider; H F Niss
Journal:  Appl Microbiol       Date:  1966-09

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 peptides containing -aminoadipic acid and cysteine in extracts of a Cephalosporium sp.

Authors:  P B Loder; E P Abraham
Journal:  Biochem J       Date:  1971-07       Impact factor: 3.857

9.  Isolation and nature of intracellular peptides from a cephalosporin C-producing Cephalosporium sp.

Authors:  P B Loder; E P Abraham
Journal:  Biochem J       Date:  1971-07       Impact factor: 3.857
  9 in total
  10 in total

1.  Elucidation of conditions allowing conversion of penicillin G and other penicillins to deacetoxycephalosporins by resting cells and extracts of Streptomyces clavuligerus NP1.

Authors:  H Cho; J L Adrio; J M Luengo; S Wolfe; S Ocran; G Hintermann; J M Piret; A L Demain
Journal:  Proc Natl Acad Sci U S A       Date:  1998-09-29       Impact factor: 11.205

2.  Comparison of the secondary metabolites in two scales of cephalosporin C (CPC) fermentation and two different post-treatment processes.

Authors:  Ying-Xiu Cao; Hua Lu; Bin Qiao; Yao Chen; Ying-Jin Yuan
Journal:  J Ind Microbiol Biotechnol       Date:  2012-10-09       Impact factor: 3.346

3.  Cell-free conversion of isopenicillin N into deacetoxycephalosporin C by Cephalosporium acremonium mutant M-0198.

Authors:  J E Baldwin; J W Keeping; P D Singh; C A Vallejo
Journal:  Biochem J       Date:  1981-02-15       Impact factor: 3.857

Review 4.  δ-(L-α-aminoadipyl)-L-cysteinyl-D-valine synthetase (ACVS): discovery and perspectives.

Authors:  Kapil Tahlan; Marcus A Moore; Susan E Jensen
Journal:  J Ind Microbiol Biotechnol       Date:  2016-10-20       Impact factor: 3.346

5.  Characterization of Streptomyces sp. strain DRS-1 and its ampicillin transformation product.

Authors:  D Roy; A Sharma; G Bhowmick; M K Roy; A C Ghosh
Journal:  Folia Microbiol (Praha)       Date:  1997       Impact factor: 2.099

6.  Cell-free conversion of delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine into an antibiotic with the properties of isopenicillin N in Cephalosporium acremonium.

Authors:  T Konomi; S Herchen; J E Baldwin; M Yoshida; N A Hunt; A L Demain
Journal:  Biochem J       Date:  1979-11-15       Impact factor: 3.857

7.  Incorporation of 3H and 14C from (6 alpha-3H)penicillin N and (10-14C,6 alpha-3H) penicillin N into deacetoxycephalosporin C.

Authors:  J E Baldwin; P D Singh; M Yoshida; Y Sawada; A L Demain
Journal:  Biochem J       Date:  1980-03-15       Impact factor: 3.857

Review 8.  Engineering deacetoxycephalosporin C synthase as a catalyst for the bioconversion of penicillins.

Authors:  Keqiang Fan; Baixue Lin; Yong Tao; Keqian Yang
Journal:  J Ind Microbiol Biotechnol       Date:  2016-11-08       Impact factor: 3.346

9.  Interference by methionine on valine uptake in Acremonium chrysogenum.

Authors:  M J Alonso; J M Luengo
Journal:  Antimicrob Agents Chemother       Date:  1987-02       Impact factor: 5.191

10.  Syntheses of penicillin N, [6 alpha-3H]penicillin N and [10-14C,6 alpha-3H]penicillin N.

Authors:  J E Baldwin; S R Herchen; P D Singh
Journal:  Biochem J       Date:  1980-03-15       Impact factor: 3.857
  10 in total

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