ENZYMATIC CONVERSION OF DEUTERATED ANALOGS OF DELTA-L-ALPHA-AMINOADIPOYL-L-CYSTEINYL-D-ALLYLGLYCINE, AN UNNATURAL SUBSTRATE FOR ISOPENICILLIN N SYNTHASE - A UNIFIED THEORY OF 2ND RING-CLOSURE
The enzyme Isopenicillin N Synthase catalyses the conversion of the modified substrate delta-L-alpha-aminoadipoyl-L-cysteinyl-D-allylglycine to six beta-lactam containing metabolites. Eight tripeptides deuterated in the allylglycine moiety have been prepared and the stereochemical course of their cyclization to the beta-lactam containing metabolites has been investigated.