title: Protecting-group-free one-pot synthesis of glycoconjugates directly from reducing sugars.
abstract: The conversion of sugars into glycomimetics typically involves multiple protecting-group manipulations. The development of methodology allowing the direct aqueous conversion of free sugars into glycosides, and mimics of oligosaccharides and glycoconjugates in a high-yielding and stereoselective process is highly desirable. The combined use of 2-azido-1,3-dimethylimidazolinium hexafluorophosphate and the Cu-catalyzed Huisgen cycloaddition allowed the synthesis of a range of glycoconjugates in a one-step reaction directly from reducing sugars under aqueous conditions. The reaction, which is completely stereoselective, may be applied to the convergent synthesis of triazole-linked glycosides, oligosaccharides, and glycopeptides. The procedure provides a method for the one-pot aqueous ligation of oligosaccharides and peptides bearing alkyne side chains.
authors.affiliation: Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140 (New Zealand).
authors.forename: David
authors.initials: D
authors.lastname: Lim
authors.forename: Margaret A
authors.initials: MA
authors.lastname: Brimble
authors.forename: Renata
authors.initials: R
authors.lastname: Kowalczyk
authors.forename: Andrew J A
authors.initials: AJ
authors.lastname: Watson
authors.forename: Antony John
authors.initials: AJ
authors.lastname: Fairbanks
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D057930:Click Chemistry / Q000379:methods*; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D006020:Glycopeptides / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
chemical_list: D002241:Carbohydrates; D006001:Glycoconjugates; D006020:Glycopeptides; D014230:Triazoles
keywords: carbohydrates; click chemistry; glycopeptides; oligosaccharide mimetics; triazoles