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Automated synthesis of oligosaccharides

  • Full or part time
  • Application Deadline
    Applications accepted all year round
  • Self-Funded PhD Students Only
    Self-Funded PhD Students Only

Project Description

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, 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,[1,2] including the recently described application of oxathiane ketal/ether-S-oxide glycosyl donors in stereoselective 1,2-cis glycosylations.[3]

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. These donors will then be showcased in the synthesis of biologically relevant carbohydrate using the Glyconeer, the UKs only automated oligosaccharide synthesiser, which is based in our lab.

All research students follow our innovative Doctoral Training in Chemistry (iDTC): cohort-based training to support the development of scientific, transferable and employability skills. All research students take the core training package which provides both a grounding in the skills required for their research, and transferable skills to enhance employability opportunities following graduation. Core training is progressive and takes place at appropriate points throughout a student’s higher degree programme, with the majority of training taking place in Year 1. In conjunction with the Core training, students, in consultation with their supervisor(s), select training related to the area of their research.

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. Chemistry at York was the first academic department in the UK to receive the Athena SWAN Gold award, first attained in 2007 and then renewed in October 2010 and in April 2015.

Funding Notes

This project is open to students who can fund their own studies or who have been awarded a scholarship separate from this project. The Chemistry Department at York is pleased to offer Wild Fund Scholarships to those from countries outside the UK. Wild Fund Scholarships offer up to full tuition fees for those from countries from outside the European Union. EU students may also be offered £6,000 per year towards living costs. For further information see: View Website

References

[1] M. A. Fascione et al, Chem. Commun., 2009, 5841-5843;
[2] M. A. Fascione et al, Carbohydr. Res., 2012, 348, 6-13;
[3] M. A. Fascione et al, Chem. Eur. J., 2012, 18, 321-333.

Related Subjects

How good is research at University of York in Chemistry?

FTE Category A staff submitted: 47.06

Research output data provided by the Research Excellence Framework (REF)

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