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The Enzymatic Synthesis of 3-Aceto-Penams Using Isopenicillin N Synthase

The Enzymatic Synthesis of 3-Aceto-Penams Using Isopenicillin N Synthase

Abstract

The synthesis of L-α-aminoadipoyl-L-cysteinyl-D-(2-amino-3-methylpropa-3,4-dienoic acid) and its subsequent incubation with isopenicillin N synthase (IPNS) was carried out. A single bicyclic product was detected by 'Hn.m.r. of the crude incubation mixture. Purification by reverse phase h.p.l.c. yielded a product assigned as a new penicillin, containing a 3-α-aceto group. The mechanism for the enzymatic conversion may be rationalised in terms of an enzyme bound iron oxene moiety (or its equivalent).
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