| EPSRC Reference: |
GR/K60961/01 |
| Title: |
STEREOSELECTIVE SYNTHESIS OF BIOLOGICALLY ACTIVE BETA- FUNCTIONALISED AMINO ACIDS USING ARYLTHIONITRO-OXIRAN |
| Principal Investigator: |
Jackson, Professor R |
| Other Investigators: |
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| Department: |
School of Chemistry |
| Organisation: |
Newcastle University |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
01 November 1995 |
Ends: |
31 October 1998 |
Value (£): |
6,246
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Summary on Grant Application Form |
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We have recently discovered a new, efficient, approach to the synthesis of beta-hydroxy alpha-amino acids. The key steps are the stereoselective epoxidation of chiral gamma-alkoxy arylthiooxiranes, followed by stereospecific reaction of these oxiranes with nitrogen nucleophiles (including ammonia) to give stereochemically defined alpha-amino thioesters. The epoxidation process can be controlled to give high selectivity in favour of either of the possible stereoisomeric products, simply by using a different epoxidising agent. This project seeks to exploit this methodology by developing stereoselective synthetic approaches to biologically significant beta-hydroxy alpha-amino acids such as the antibiotic obafluorin, for example. We also intend to extend the methodology by developong approaches to the stereocontrolled synthesis of beta-amino alpha-hydroxy acides and alpha, beta-diamino acids. Further investigation of the methodology, including the use of other nucleophilic epoxidising agents, will be also be carried out.
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Key Findings |
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This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
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Potential use in non-academic contexts |
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This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
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Impacts |
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| Description |
This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk |
| Summary |
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| Date Materialised |
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Sectors submitted by the Researcher |
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This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
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| Project URL: |
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| Further Information: |
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| Organisation Website: |
http://www.ncl.ac.uk |