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ISOPENICILLIN-N SYNTHASE - A NEW MODE OF REACTIVITY

Abstract:

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-valine] 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-di...

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Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
TETRAHEDRON
Volume:
48
Issue:
41
Pages:
9085-9100
Publication date:
1992-10-09
DOI:
ISSN:
0040-4020
URN:
uuid:825311f1-8daf-4787-84b3-32d107ffbbb3
Source identifiers:
43967
Local pid:
pubs:43967

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