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Chemical glycobiology: new methods for stereoselective and automated glycosylations in the synthesis of biologically relevant carbohydrate probes

Department of Chemistry

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About the Project

Carbohydrates play important roles in a number of biological processes including tumour metastasis, bacterial and viral recognition, and the immunological response. Following the sequencing of the human genome 12 years ago, breakthroughs in the field have stimulated a ‘chemical glycobiology’ research boom, which has undoubtedly yielded stunning results but also served to highlight how little we still understand about the roles of carbohydrates in all domains of life. To address the most important questions that remain unanswered in the field, it is essential more efficient and stereoselective methods for the synthesis of biologically relevant carbohydrates probes are developed.

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.

All Chemistry research students have access to our innovative Doctoral Training in Chemistry (iDTC): cohort-based training to support the development of scientific, transferable and employability skills:

The Department of Chemistry holds an Athena SWAN Gold Award and is committed to supporting equality and diversity for all staff and students. The Department strives to provide a working environment which allows all staff and students to contribute fully, to flourish, and to excel:

You should expect hold or expect to achieve the equivalent of at least a UK upper second class degree in Chemistry or a related subject. Please check the entry requirements for your country:

Funding Notes

This project is available to students from any country who can fund their own studies. The Department of Chemistry at the University of York is pleased to offer Wild Fund Scholarships. Applications are welcomed from those who meet the PhD entry criteria from any country outside the UK. Scholarships will be awarded on supervisor support, academic merit, country of origin, expressed financial need and departmental strategy. For further details and deadlines, please see our website:
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