γ-Lactam formation from tripeptides with isopenicillin N synthase

Abstract
Incubation of isopenicillin N synthase (IPNS) with analogues of the natural substrate [(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine (2) in which the cysteinyl residue was replaced by homocysteine gave epimeric 5-hydroxy γ-lactams (10), with no evidence for the formation of bicyclic products.

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