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EPSRC Reference: GR/N37001/01
Title: SYNTHESIS OF THE THIOPEPTIDE AMYTHIAMYCIN A, A HETEROCYCLIC PEPTIDE MACROCYCLE
Principal Investigator: Moody, Professor CJ
Other Investigators:
Researcher Co-Investigators:
Project Partners:
Department: Chemistry
Organisation: University of Exeter
Scheme: Standard Research (Pre-FEC)
Starts: 15 January 2001 Ends: 14 January 2004 Value (£): 171,382
EPSRC Research Topic Classifications:
Biological & Medicinal Chem.
EPSRC Industrial Sector Classifications:
Pharmaceuticals and Biotechnology Chemicals
Related Grants:
Panel History:  
Summary on Grant Application Form
The thiopeptide antibiotics, exemplified by micrococcin and related compounds, are a growing class of sulphur containing modified cyclic peptides that inhibit protein synthesis in Gram positive bacteria, and show promising activity against multiply resistant bacteria and against the malaria parasite.It is proposed to develop routes to these biologically important compounds as exemplified by the synthesis of amythiamycin A. Two routes are proposed: a coupling of pyridine and thiazole containing fragments, and a novel biomimetic approach in which the pyridine ring is formed last.To synthesise the thiazole rings, the addition of metallo-thiazoles to chiral oxime ether will be investigated as will a new carbenoid method, based on highly chemoselective N-H insertion reactions. The pyridine unit will be accessed by a coupling between an enamine and a ynone, and the various fragments will be coupled together using peptide coupling techniques.In parallel, it is proposed to investigate an entirely different approach to the pyridine unit of amythiamycin A. The approach is bimimetic and is based on a suggestion that the pyridine ring in the thiopeptides arises from coupling of two dehydroalanine residues.
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