Tetrahedron p. 9085 - 9100 (1992)
Update date:2022-07-30
Topics:
Baldwin, Jack E.
Lynch, Gregory P.
Schofield, Christopher J.
Incubation of L-δ-(α-aminoadipoyl)-L-(3,3-difluorohomocysteinyl)-D-valine [an analogue of the natural substrate: L-δ-(α-aminoadipoyl)-L-(cysteinyl)-D-varine] with isopenicillin N synthase (IPNS) resulted in the production of a thiocarboxylic acid, i.e. both equivalents of the dioxygen cosubstrate were utilised to oxidise a single carbon of the cysteinyl analogue. This result and others are rationalised in terms of mechanistic proposals for the first ring closure by IPNS. The synthesis of L-difluorohomocysteine and related structures, via 3,3-difluoro-β-lactams, is described.
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