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Biomimetic synthesis of lantibiotics

Burrage, S., Raynham, T., Williams, G., Essex, J. W., Allen, C., Cardno, M., Swali, V. and Bradley, M. (2000) Biomimetic synthesis of lantibiotics Chemistry - A European Journal, 6, (8), pp. 1455-1466. (doi:10.1002/(SICI)1521-3765(20000417)6:8<1455::AID-CHEM1455>3.0.CO;2-M).

Record type: Article

Abstract

The lantibiotics are a class of highly posttranslationally modified small peptide antibiotics containing numerous lanthionine and dehydroamino acid residues. We have prepared peptides containing multiple dehydroamino acids and cysteine residues in order to probe the biomimetic synthesis of the lantibiotics from their precursor peptides. A novel synthetic methodology was developed to allow the synthesis of multiple dehydroamino acid containing peptides. Cyclisations were rapid, quantitative and regiospecific, Remarkably the peptide sequences alone appear to contain sufficient information to direct a series of stereo- and regiospecific ring closures. Thus both thr two linear peptides for the B and E-rings closed stereoselectively. In the case of the A-ring precursor peptide which contained two dehydroamino acids, cyclisation was again totally regioselective, although not totally stereoselective.

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More information

Published date: 14 April 2000
Keywords: biomimetic synthesis, lantibiotics, peptides, solid-phase synthesis peptide antibiotic nisin, amino-acids, nmr, dehydroalanine, biosynthesis, ring, expression, prepeptide, epidermin, precursor

Identifiers

Local EPrints ID: 19070
URI: http://eprints.soton.ac.uk/id/eprint/19070
ISSN: 0947-6539
PURE UUID: 2480f6ce-5b3b-476b-aa51-cd40c26ca85c

Catalogue record

Date deposited: 18 Jan 2006
Last modified: 17 Jul 2017 16:33

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Contributors

Author: S. Burrage
Author: T. Raynham
Author: G. Williams
Author: J. W. Essex
Author: C. Allen
Author: M. Cardno
Author: V. Swali
Author: M. Bradley

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