title: Solid-phase synthesis of thioether-linked glycopeptide mimics for application to glycoprotein semisynthesis.
abstract: [reaction: see text]. Glycoproteins are particularly suited to protein semisynthesis since homogeneous samples for biological analyses are not readily available using traditional recombinant techniques. Here we apply glycosyl iodoacetamides, normally used for the modification of bacterially derived proteins, to solid-phase glycopeptide synthesis. This provides access to glycopeptide alpha-thioesters, which may lend themselves to the semisynthesis of homogeneous N-linked glycoprotein mimics and novel glycopeptide libraries.
authors.affiliation: Department of Chemistry, University of Edinburgh, Kings Buildings, West Mains Road, Edinburgh EH9 3JJ, Scotland. derek.macmillan@ed.ac.uk
authors.forename: Derek
authors.initials: D
authors.lastname: Macmillan
authors.forename: Alison M
authors.initials: AM
authors.lastname: Daines
authors.forename: Monika
authors.initials: M
authors.lastname: Bayrhuber
authors.forename: Sabine L
authors.initials: SL
authors.lastname: Flitsch
mesh_terms: D002851:Chromatography, High Pressure Liquid; D003545:Cysteine / Q000737:chemistry; D006020:Glycopeptides / Q000737:chemistry*; D006023:Glycoproteins / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008956:Models, Chemical; D018716:Molecular Mimicry; D021241:Spectrometry, Mass, Electrospray Ionization; D013438:Sulfhydryl Compounds / Q000737:chemistry
chemical_list: D006020:Glycopeptides; D006023:Glycoproteins; D007202:Indicators and Reagents; D013438:Sulfhydryl Compounds; D003545:Cysteine