Direct aqueous synthesis of cyanomethyl thioglycosides from reducing sugars; ready access to reagents for protein glycosylation.
Unprotected carbohydrates can be directly converted into cyanomethyl thioglycosides in a completely stereoselective manner by reaction with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and mercaptoacetonitrile in aqueous solution in the presence of triethylamine. Reaction with methoxide provides 2-imino-2-methoxyethyl (IME) thioglycosides, which may be used directly for the glycosylation of surface protein lysine residues.
Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand. antony.fairbanks@canterbury.ac.nz.
Stewart R
SR
Alexander
Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand. antony.fairbanks@canterbury.ac.nz and Biomolecular Interaction Centre, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand.
Antony J
AJ
Fairbanks
D000818:Animals; D002645:Chickens; D006031:Glycosylation; D054879:Halogenation; D007202:Indicators and Reagents / Q000138:chemical synthesis / Q000737:chemistry; D008239:Lysine / Q000737:chemistry; D008745:Methylation; D008958:Models, Molecular; D009113:Muramidase / Q000737:chemistry; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D011506:Proteins / Q000737:chemistry*; D013865:Thioglycosides / Q000138:chemical synthesis* / Q000737:chemistry
D007202:Indicators and Reagents; D009570:Nitriles; D009844:Oligosaccharides; D011506:Proteins; D013865:Thioglycosides; D009113:Muramidase; D008239:Lysine