NEW PENICILLINS FROM ISOPENICILLIN N SYNTHASE.

Article abstract of DOI:10.1016/S0040-4020(01)87142-8

The three tripeptides δ-L-α-aminoadipoyl-L-cysteinyl-D-propargylglycine, δ-L-α-aminoadipoyl-L-cysteinyl-D-cyanoalanine and δ-L-α-aminoadipoyl-L-cysteinyl-D-<4,4,5,5-2H4>-norvaline were synthesised and incubated with the enzyme Isopenicillin N Synthase (IPNS).All incubation mixtures contained biologically active products, and led to the isolation of four new penicillins (β-ethyl, α-acetylenic, α- and β-nitrile) following purification by reverse phase HPLC.The stereochemistries of formation of monosubstituted penicillins with IPNS are rationalised.