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

J Ind Microbiol Biotechnol. 2017 May;44(4-5):705-710. doi: 10.1007/s10295-016-1857-0. Epub 2016 Nov 8.

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.

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

Publication types

  • Review

MeSH terms

  • Biocatalysis*
  • Cephalosporins / biosynthesis*
  • Cephalosporins / metabolism
  • Escherichia coli / genetics
  • Escherichia coli / metabolism
  • Penicillin G / metabolism
  • Penicillins / biosynthesis*
  • Penicillins / metabolism
  • Substrate Specificity

Substances

  • Cephalosporins
  • Penicillins
  • deacetoxycephalosporin C
  • 7-aminodesacetoxycephalosporanic acid
  • Penicillin G