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

Mustapa, MFM; Harris, R; Esposito, D; Chubb, NAL; Mould, J; Schultz, D; Driscoll, PC; (2003) Synthesis of a cyclic peptide containing norlanthionine: Effect of the thioether bridge on peptide conformation. J ORG CHEM , 68 (21) 8193 - 8198. 10.1021/jo0346407.

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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.

Type: Article
Title: Synthesis of a cyclic peptide containing norlanthionine: Effect of the thioether bridge on peptide conformation
DOI: 10.1021/jo0346407
Keywords: SOLID-PHASE SYNTHESIS, LANTIBIOTIC NISIN, BIOLOGICAL-ACTIVITIES, NMR-SPECTROSCOPY, QUANTUM NMR, LANTHIONINE, VANCOMYCIN, DESIGN, BIOSYNTHESIS, CYCLIZATION
UCL classification: UCL > School of Life and Medical Sciences
UCL > School of Life and Medical Sciences > Faculty of Life Sciences
UCL > School of Life and Medical Sciences > Faculty of Life Sciences > Biosciences (Division of)
UCL > School of BEAMS > Faculty of Maths and Physical Sciences
UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry
URI: http://discovery.ucl.ac.uk/id/eprint/156299
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