Incubation of [(5S)-5-amino-5-carboxypentanoyl]-L-[3-13C]cysteinyl-D-[15N,3-2H]valine with isopenicillin N synthase (IPNS) resulted in the observation of a ‘shunt metabolite’, which we believe is formed from the collapse of an enzyme-bound monocyclic β-lactam intermediate, and which from chemical studies has been shown not to be derived from the decomposition of a free thiol monocyclic β-lactam.
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Baldwin et al. (1988) studied this question.
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