Solid-phase synthesis of thioether-linked glycopeptide mimics for application to glycoprotein semisynthesis.
[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.
Macmillan
Derek
D
Department of Chemistry, University of Edinburgh, Kings Buildings, West Mains Road, Edinburgh EH9 3JJ, Scotland. derek.macmillan@ed.ac.uk
Daines
Alison M
AM
Bayrhuber
Monika
M
Flitsch
Sabine L
SL
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
D006020:Glycopeptides; D006023:Glycoproteins; D007202:Indicators and Reagents; D013438:Sulfhydryl Compounds; D003545:Cysteine