title: Synthesis of the antimicrobial S-linked glycopeptide, glycocin F.
abstract: The first total synthesis of glycocin F, a uniquely diglycosylated antimicrobial peptide bearing a rare S-linked N-acetylglucosamine (GlcNAc) moiety in addition to an O-linked GlcNAc, has been accomplished using a native chemical ligation strategy. The synthetic and naturally occurring peptides were compared by HPLC, mass spectrometry, NMR and CD spectroscopy, and their stability towards chymotrypsin digestion and antimicrobial activity were measured. This is the first comprehensive structural and functional comparison of a naturally occurring glycocin with an active synthetic analogue.
authors.affiliation: School of Chemical Sciences, The University of Auckland, 23 Symonds St., Auckland 1142 (New Zealand); Maurice Wilkins Centre for Molecular Biodiscovery, School of Biological Sciences, The University of Auckland, Auckland 1142 (New Zealand). m.brimble@auckland.ac.nz.
authors.forename: Margaret A
authors.initials: MA
authors.lastname: Brimble
authors.forename: Pat J
authors.initials: PJ
authors.lastname: Edwards
authors.forename: Paul W R
authors.initials: PW
authors.lastname: Harris
authors.forename: Gillian E
authors.initials: GE
authors.lastname: Norris
authors.forename: Mark L
authors.initials: ML
authors.lastname: Patchett
authors.forename: Tom H
authors.initials: TH
authors.lastname: Wright
authors.forename: Sung-Hyun
authors.initials: SH
authors.lastname: Yang
authors.forename: Sarah E
authors.initials: SE
authors.lastname: Carley
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001430:Bacteriocins / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000890:Anti-Infective Agents; D001430:Bacteriocins; D006020:Glycopeptides; D010455:Peptides; C557037:glycocin F, Lactobacillus plantarum
keywords: antimicrobial peptides; disulfide; glycocin F; glycopeptides; glycosylation