Cephalosporin C biosynthesis; stereochemistry of the incorporation ofD,L,D-α-aminodipoyl-cysteinyl-(3S)-[2-2H,4-13C]valine into β-lactam compounds

Abstract

Listen

Translate article

Incubation of D,L,D-α-Aminodipoyl-cysteinyl-(3S)-[2-2H,4-13C]valine (8b) with partially purified isopenicilln N synthetase fromCephalosporium acremonium CO 728 gave stereospecifically labelled (2R,3S)-[2′-13C,3-2H]penicillin N(9): further incubation of the product with partially purified deacetoxycephalosporin C/ deacetylcephalosporin C synthetase from C. acremonium CO 728 gave ring expanded products in which the 13C-label was incorporated exclusively into the C3′-exocyclic positions.