Enabling methodology for the end functionalisation of glycosaminoglycan oligosaccharides

Emiliano Gemma, Odile Meyer, Dušan Uhrín, Alison N. Hulme
2008 Molecular Biosystems  
AN 2008, 'Enabling methodology for the end functionalisation of glycosaminoglycan oligosaccharides' Abbreviations: Abbreviations used in this review, are as follows: GlcNAc = N-acetyl-D-glucosamine, GalNAc = Nacetyl-D-galactosamine, GlcA = D-glucuronic acid, IdoA = L-iduronic acid, ΔUA = 4-deoxy-L-threohex-4-enopyranosyluronic acid, GlcNS = N-sulfo-D-glucosamine, GlcNS(6S) = N-sulfo-6-O-sulfo-Dglucosamine, IdoA(2S) = 2-O-sulfo-L-iduronic acid, ΔUA(2S) =
more » ... luronic acid. Graphical abstract: Post-print of peer-reviewed article published by the Royal Society of Chemistry. . (2008). Enabling methodology for the end functionalisation of glycosaminoglycan oligosaccharides. Molecular Biosystems, 4(6), 481-495. Abstract The chemical functionalisation of glycosaminoglycans is very challenging due to their structural heterogeneity and polyanionic character; but as an enabling technology it promises rich rewards in terms of the structural and biological data it will afford. This review surveys the known methods for the preparation of glycosaminoglycan oligosaccharides and conditions for the selective functionalisation of both the reducing and non-reducing ends. The synthetic merits of each approach are discussed, together with the structural modification of the glycosaminoglycan oligosaccharide which they confer. Recent applications of this methodology are highlighted, including introduction of functional labels for gel mobility shift assays and NMR studies of glycosaminoglycan-protein complexes, and synthesis of immobilised glycosaminoglycan arrays
doi:10.1039/b801666f pmid:18493641 fatcat:k4jdrq3l5fa4vfzihg3o2wxwny