Saccharide Thiols for the Synthesis of S-Linked Glycosaminoglycan Analogues

PS1 Poster session 1 Odd numbers
Location (hall): 
Start/end time: 
Monday, July 1, 2019 - 15:45 to 17:15

Elizabeth Grayson1, Benjamin Davis2

1Durham University, Durham, United Kingdom, 2University 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

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