title: Synthesis of a cyclic peptide containing norlanthionine: effect of the thioether bridge on peptide conformation.
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.
authors.affiliation: Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon Street, London WC1H OAJ, UK.
authors.forename: M Firouz
authors.initials: MF
authors.lastname: Mohd Mustapa
authors.forename: Richard
authors.initials: R
authors.lastname: Harris
authors.forename: Diego
authors.initials: D
authors.lastname: Esposito
authors.forename: Nathan A L
authors.initials: NA
authors.lastname: Chubb
authors.forename: Jessica
authors.initials: J
authors.lastname: Mould
authors.forename: Darren
authors.initials: D
authors.lastname: Schultz
authors.forename: Paul C
authors.initials: PC
authors.lastname: Driscoll
authors.forename: Alethea B
authors.initials: AB
authors.lastname: Tabor
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry*; D001952:Bridged-Ring Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009561:Nisin / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D011487:Protein Conformation; D013237:Stereoisomerism; D013440:Sulfides / Q000737:chemistry*
chemical_list: D001952:Bridged-Ring Compounds; D010456:Peptides, Cyclic; D013440:Sulfides; D009561:Nisin; C001520:lanthionine; D000409:Alanine