Synthesis of a cyclic peptide containing norlanthionine: effect of the thioether bridge on peptide conformation

M Firouz Mohd Mustapa; Richard Harris; Diego Esposito; Nathan A L Chubb; Jessica Mould; Darren Schultz; Paul C Driscoll; Alethea B Tabor

doi:10.1021/jo0346407

Synthesis of a cyclic peptide containing norlanthionine: effect of the thioether bridge on peptide conformation

J Org Chem. 2003 Oct 17;68(21):8193-8. doi: 10.1021/jo0346407.

Authors

M Firouz Mohd Mustapa¹, Richard Harris, Diego Esposito, Nathan A L Chubb, Jessica Mould, Darren Schultz, Paul C Driscoll, Alethea B Tabor

Affiliation

¹ Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon Street, London WC1H OAJ, UK.

PMID: 14535803
DOI: 10.1021/jo0346407

Abstract

Two diastereomeric analogues of ring C of nisin incorporating a novel norlanthionine residue have been synthesized via a triply orthogonal protecting group strategy. A full structural study was carried out by NMR, which elucidated the conformational properties of the two peptides and enabled the identity of each diastereoisomer to be proposed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alanine / analogs & derivatives*
Alanine / chemistry*
Bridged-Ring Compounds / chemistry*
Molecular Structure
Nisin / chemistry
Peptides, Cyclic / chemical synthesis*
Peptides, Cyclic / chemistry
Protein Conformation
Stereoisomerism
Sulfides / chemistry*

Substances

Bridged-Ring Compounds
Peptides, Cyclic
Sulfides
Nisin
lanthionine
Alanine