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), 1455-1466. (doi: 10.1002/(SICI)1521-3765(20000417)6:8<1455::AID-CHEM1455>3.0.CO;2-M).

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Description/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.

Item Type: Article
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Keywords: biomimetic synthesis, lantibiotics, peptides, solid-phase synthesis peptide antibiotic nisin, amino-acids, nmr, dehydroalanine, biosynthesis, ring, expression, prepeptide, epidermin, precursor
Subjects: Q Science
Q Science > QD Chemistry
Divisions: University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 19070
Date Deposited: 18 Jan 2006
Last Modified: 27 Mar 2014 18:08
URI: http://eprints.soton.ac.uk/id/eprint/19070

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