ORGN 688 |
Synthetic studies towards the heterocyclic building blocks of the thiopeptide antibiotics
| SP Thompson1, R.A. Hughes1, Christopher J Moody2, and Lilian Alcaraz3. (1) School of Biological and Chemical Sciences, University of Exeter, University of Exeter, Stocker Road, Exeter, EX4 7HR, United Kingdom, (2) School of Chemistry, University of Exeter, Stocker Road, Exeter EX4 4QD, United Kingdom, (3) Department of Medicinal Chemistry, AstraZeneca R&D Charnwood, Bakewell Road, Loughborough LE11 5RH, United Kingdom |
| The thiopeptide antibiotics are a class of sulphur containing highly modified cyclic peptides, characterised by several common structural features: the presence of thiazole and in some cases, oxazole rings, unusual and dehydroamino acids and a heterocyclic centrepiece of a tri- or tetra-substituted pyridine all in a macrocyclic array. The amythiamicins were isolated in 1994 by Shimanaka and coworkers from the fermentation broth of Amycolatopsis sp. MI481-42F4 and have been shown to inhibit the growth of Gram-positive bacteria including multi-drug resistant strains. This poster describes synthetic studies towards the pyridine heterocyclic core, via the above proposed biomimetic cycloaddition method of serine derived 1-alkoxy-2-azadienes with dehydroalanine derivatives, and the synthesis of other fragments of the amythiamycins A. 
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New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- Hall D, Sci-Mix
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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