Literature DB >> 27826726

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

Keqiang Fan1, Baixue Lin2, Yong Tao2, Keqian Yang3.   

Abstract

7-aminodeacetoxycephalosporanic acid (7-ADCA) is a key intermediate of many clinically useful semisynthetic cephalosporins that were traditionally prepared by processes involving chemical ring expansion of penicillin G. Bioconversion of penicillins to cephalosporins using deacetoxycephalosporin C synthase (DAOCS) is an alternative and environmentally friendly process for 7-ADCA production. Arnold Demain and co-workers pioneered such a process. Later, protein engineering efforts to improve the substrate specificity and catalytic efficiency of DAOCS for penicillins have been made by many groups, and a whole cell process using Escherichia coli for bioconversion of penicillins has been developed.

Entities:  

Keywords:  7-aminodeacetoxycephalosporanic acid (7-ADCA); Bioconversion; Deacetoxycephalosporin C synthase (DAOCS); Penicillin G; Penicillin expandase

Mesh:

Substances:

Year:  2016        PMID: 27826726     DOI: 10.1007/s10295-016-1857-0

Source DB:  PubMed          Journal:  J Ind Microbiol Biotechnol        ISSN: 1367-5435            Impact factor:   3.346


  39 in total

1.  Alteration of the co-substrate selectivity of deacetoxycephalosporin C synthase. The role of arginine 258.

Authors:  H J Lee; M D Lloyd; I J Clifton; K Harlos; A Dubus; J E Baldwin; J M Frere; C J Schofield
Journal:  J Biol Chem       Date:  2001-02-21       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.  Iterative combinatorial mutagenesis as an effective strategy for generation of deacetoxycephalosporin C synthase with improved activity toward penicillin G.

Authors:  Junjie Ji; Keqiang Fan; Xiuyun Tian; Xia Zhang; Yuxiu Zhang; Keqian Yang
Journal:  Appl Environ Microbiol       Date:  2012-08-24       Impact factor: 4.792

4.  Purification and initial characterization of deacetoxycephalosporin C synthase from Streptomyces clavuligerus.

Authors:  M J Rollins; D W Westlake; S Wolfe; S E Jensen
Journal:  Can J Microbiol       Date:  1988-11       Impact factor: 2.419

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

Authors:  M Yoshida; T Konomi; M Kohsaka; J E Baldwin; S Herchen; P Singh; N A Hunt; A L Demain
Journal:  Proc Natl Acad Sci U S A       Date:  1978-12       Impact factor: 11.205

6.  Stimulatory effect of growth in the presence of alcohols on biotransformation of penicillin G into cephalosporin-type antibiotics by resting cells of Streptomyces clavuligerus NP1.

Authors:  M J Fernández; J L Adrio; J M Piret; S Wolfe; S Ro; A L Demain
Journal:  Appl Microbiol Biotechnol       Date:  1999-10       Impact factor: 4.813

7.  Reconstitution of TCA cycle with DAOCS to engineer Escherichia coli into an efficient whole cell catalyst of penicillin G.

Authors:  Baixue Lin; Keqiang Fan; Jian Zhao; Junjie Ji; Linjun Wu; Keqian Yang; Yong Tao
Journal:  Proc Natl Acad Sci U S A       Date:  2015-07-27       Impact factor: 11.205

8.  Family shuffling of expandase genes to enhance substrate specificity for penicillin G.

Authors:  Jyh-Shing Hsu; Yunn-Bor Yang; Chan-Hui Deng; Chia-Li Wei; Shwu-Huey Liaw; Ying-Chieh Tsai
Journal:  Appl Environ Microbiol       Date:  2004-10       Impact factor: 4.792

9.  Purification and initial characterization of an enzyme with deacetoxycephalosporin C synthetase and hydroxylase activities.

Authors:  J E Baldwin; R M Adlington; J B Coates; M J Crabbe; N P Crouch; J W Keeping; G C Knight; C J Schofield; H H Ting; C A Vallejo
Journal:  Biochem J       Date:  1987-08-01       Impact factor: 3.857

10.  Improved expression of a hybrid Streptomyces clavuligerus cefE gene in Penicillium chrysogenum.

Authors:  S W Queener; R J Beckmann; C A Cantwell; R L Hodges; D L Fisher; J E Dotzlaf; W K Yeh; D McGilvray; M Greaney; P Rosteck
Journal:  Ann N Y Acad Sci       Date:  1994-05-02       Impact factor: 5.691

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  2 in total

Review 1.  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

2.  Deacetoxycephalosporin C synthase (expandase): Research progress and application potential.

Authors:  Xiaofan Niu; Jian Zhang; Xianli Xue; Depei Wang; Lin Wang; Qiang Gao
Journal:  Synth Syst Biotechnol       Date:  2021-11-23
  2 in total

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