Synthesis of a cyclic peptide containing norlanthionine: effect of the thioether bridge on peptide conformation.
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.
Mohd Mustapa
M Firouz
MF
Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon Street, London WC1H OAJ, UK.
Harris
Richard
R
Esposito
Diego
D
Chubb
Nathan A L
NA
Mould
Jessica
J
Schultz
Darren
D
Driscoll
Paul C
PC
Tabor
Alethea B
AB
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*
D001952:Bridged-Ring Compounds; D010456:Peptides, Cyclic; D013440:Sulfides; D009561:Nisin; C001520:lanthionine; D000409:Alanine