The conversion of the tripeptide δ-L-α-aminoadipolyl-L-cysteinyl-D-valine into isopenicillin N catalysed by the enzyme isopenicillin N synthetase has been shown to occur with complete retention of the cysteinyl 3-pro-R-hydrogen and with complete loss of the cysteinyl 3-pro-S-hydrogen [δ-L-α-aminoadipoyl = 5-(5S)-amino-5-carboxypentanoyl].
J. E. Baldwin, R. M. Adlington, N. G. Robinson and H. Ting, J. Chem. Soc., Chem. Commun., 1986, 409 DOI: 10.1039/C39860000409
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