Stereoselective synthesis of glycosides
Lead Research Organisation:
University of Bristol
Department Name: Chemistry
Abstract
2-Deoxyglycosides are an important class of carbohydrates which are devoid of functionality at the C 2 position. This ubiquitous class of chiral acetals are found in various natural products, such as the anticancer compounds Landomycin A and Lomaiviticin A. The challenges for their synthesis include the fact that most stereoselective glycosylations employ a group at C-2 to direct nucleophilic attack via neighbouring group participation, making such methods inapplicable. A general approach based on reagent-controlled rather than substrate-controlled glycosylation to achieve stereoselectivity would therefore be an important development.
To this end, we propose the development of new catalytic methods for the stereoselective generation of alpha- and beta-glycosides, and the subsequent use of such protocols in the synthesis of biologically-relevant oligosaccharides. We intend to develop generally applicable methods for the synthesis of all types of glycosides, including 2 deoxyglycosides, 2,6-deoxyglucosides, 2-deoxy-2-aminoglycosides and (through our collaborators in Illinois) sialilated glycosides, a class of carbohydrates for which no general methods for achieving stereocontrol exist.
To this end, we propose the development of new catalytic methods for the stereoselective generation of alpha- and beta-glycosides, and the subsequent use of such protocols in the synthesis of biologically-relevant oligosaccharides. We intend to develop generally applicable methods for the synthesis of all types of glycosides, including 2 deoxyglycosides, 2,6-deoxyglucosides, 2-deoxy-2-aminoglycosides and (through our collaborators in Illinois) sialilated glycosides, a class of carbohydrates for which no general methods for achieving stereocontrol exist.
Organisations
Publications
Jeanneret RA
(2020)
Conformationally Constrained Glycosyl Donors as Tools to Control Glycosylation Outcomes.
in The Journal of organic chemistry
Studentship Projects
Project Reference | Relationship | Related To | Start | End | Student Name |
---|---|---|---|---|---|
EP/N509619/1 | 30/09/2016 | 29/09/2021 | |||
2131623 | Studentship | EP/N509619/1 | 30/09/2018 | 29/09/2022 | Simon Johnson |
EP/R513179/1 | 30/09/2018 | 29/09/2023 | |||
2131623 | Studentship | EP/R513179/1 | 30/09/2018 | 29/09/2022 | Simon Johnson |
Description | The research I have been conducting over the past ca. 18 months concerns making unnatural versions of complex carbohydrates, used by the body in a variety of biological pathways. These have been found to play a crucial role in the mediation of inflammatory disease pathways such as cancer. The ongoing research is progressing towards studying the interaction of these carbohydrates in their intended biological system, following the recent successful synthesis of a series of compounds with which these tests can be conducted. |
Exploitation Route | An understanding of these carbohydrate interactions may allow other specialists in the field (particularly towards the biological aspects of the project) to further progress research into the therapeutic uses of such molecules, ultimately leading to the design, synthesis and testing of analogues which allow for closer/more efficient studies into disease pathways. |
Sectors | Chemicals,Pharmaceuticals and Medical Biotechnology |
Description | RSC Twitter Poster Conference 2021 |
Form Of Engagement Activity | Engagement focused website, blog or social media channel |
Part Of Official Scheme? | No |
Geographic Reach | International |
Primary Audience | Postgraduate students |
Results and Impact | An RSC-hosted digital poster conference, in which postgraduate students and Early Careers Researchers disseminated their research to an international audience of their peers. There were open discussions about future plans and the content of the poster with a panel of judges/subject chairs and between participants. |
Year(s) Of Engagement Activity | 2021 |
URL | https://twitter.com/SiJo95/status/1366719952816902150?s=20 |