About the Project
Whilst nature utilises the exquisite specificity of glycosyltransferases to control the stereochemistry of new glycosidic bonds, synthetic chemists have strived for decades to develop equally elegant strategies to achieve the same goal in the flask. Within this puzzle, the stereoselective synthesis of 1,2-cis glycosides is a particularly elusive piece. Much recent work in this field has revolved around the study of stabilised glycosyl sulfonium ions and their stereodirecting ability, including the recently described application of oxathiane ketal/ether-S-oxide glycosyl donors in stereoselective 1,2-cis glycosylations. In a representative example of the research undertaken in our group, we propose to develop new variants of these oxathiane glycosyl donor scaffolds that undergo stereoselective glycosylation to afford both 1,2-cis and 1,2-trans glycosides. We also aim to deploy these novel methods in automated glycan assembly strategies, using the Glyconeer, the UK’s only automated oligosaccharide synthesiser housed in our lab in York. These strategies will then be showcased in the synthesis of biologically relevant carbohydrate motifs to be used as probes in interdisciplinary ‘chemical glycobiology’ studies.
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