| EPSRC Reference: |
GR/R25934/01 |
| Title: |
Stereospecific Synthesis of C-Glycosides, C-Glycopeptides and C-Oligosaccharides |
| Principal Investigator: |
Fairbanks, Professor AJ |
| Other Investigators: |
|
| Researcher Co-Investigators: |
|
| Project Partners: |
|
| Department: |
Oxford Chemistry |
| Organisation: |
University of Oxford |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
01 September 2001 |
Ends: |
31 August 2004 |
Value (£): |
75,162
|
| EPSRC Research Topic Classifications: |
| Carbohydrate Chemistry |
Chemical Synthetic Methodology |
|
| EPSRC Industrial Sector Classifications: |
| Pharmaceuticals and Biotechnology |
No relevance to Underpinning Sectors |
|
| Related Grants: |
|
| Panel History: |
|
|
Summary on Grant Application Form |
|
The project will focus on the further development of our recently disclosed tandem approach to the stereoselective synthesis of C-glycosides using ester methylenation followed by Claisen rearrangement. The project starting point will be the facile synthesis of a series of a C-glycosides by simple extension of our existing protocols. This will provide an excellent entry for the new graduate student and allow optimisation of reaction conditions with the caveat of preservation of anomeric integrity, by investigation of more efficient protocols to replace the Tebbe methylenation, and catalysis of the Claisen reaction to avoid the use of high temperatures. The project will then be developed along the following themes.The use of amino acids as coupling partners to allow the synthesis of C-glycosyl amino acids and ultimately C-glycopeptides. The use of carbohydrates as coupling partners to allow the synthesis of C-disaccharides and ultimately C-oligosaccharides. The use of different building blocks will allow assemble to be performed in a parallel synthetic manner. Investigations into complete re-oxygenation of the sugar ring, and also of introduction of nitrogen, allowing access to C-glycosyl amino sugars. Development of new methodology for the stereospecific construction of disubstituted C-glycosides by initial glycal alkylation. The investigation of the feasibility of carrying out optimised reactions on the solid phase.
|
|
Key Findings |
|
This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
|
|
Potential use in non-academic contexts |
|
This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
|
|
Impacts |
|
| Description |
This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk |
| Summary |
|
| Date Materialised |
|
|
|
|
Sectors submitted by the Researcher |
|
This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
|
| Project URL: |
|
| Further Information: |
|
| Organisation Website: |
http://www.ox.ac.uk |