Saccharide Thiols for the Synthesis of S-Linked Glycosaminoglycan Analogues

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1st EuroCarb Young Researcher (ECYR) Workshop

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Mini symposium: Glycobiology at the LUMC and beyond

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Saccharide Thiols for the Synthesis of S-Linked Glycosaminoglycan Analogues

Elizabeth Grayson 1 , Benjamin Davis 2

1 Durham University, Durham, United Kingdom, 2 University of Oxford, Oxford, United Kingdom

Glycosaminoglycans (GAGs) are an important group of biomolecules and are unbranched polysaccharides consisting of repeating disaccharide moieties. One GAG, heparin, is polysulfated with alternating D-glucosamino and either D-glucuronic or L-iduronic acid units and is used as an anticoagulant drug.[1] As part of our work on heparin analogues in which the disaccharide units are S-linked rather than O-linked, we are attempting to synthesize the disaccharide thiol 5. (see Scheme below). The donor 1 is synthesized starting from glucose pentaacetate and the acceptor 2 from glucosamine hydrochloride The disaccharide 3 obtained from the glycosylation reaction between 1 and 2 has been subjected to multistep manipulations to give 4, a possible precursor to the desired thiol 5.

Progress towards the target disaccharide thiol 5

I. Capila and R. J. Linhart, Angew. Chem. Int. Ed., 2002, 114, 426-450.

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