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Content archived on 2024-05-27

Application of Lithiated Carbamates to the Asymmetric Synthesis of Sulfolipid-I

Objective

"Mycobacterium tuberculosis, the causative agent of human tuberculosis, is unique among bacterial pathogens. Sulfolipid-I (SL-I) is the major constituent metabolite of thick cell wall present in Mycobacterium Tuberculosis (M-TB). SL-I comprises of a disaccharide and four chiral hydrophobic lipid substituents, the overall structure of which is responsible for the resistance of M. Tuberculosis to antibiotics. While SL-I has been shown to elicit specific responses from immune cells, the mechanistic basis of these effects, biosynthesis and biological activities are unknown. Although a number of studies have been reported on the synthesis of disaccharide core and hydrophobic lipids of SL-I, major challenges reside in the synthesis of chiral hydrophobic lipids, which comprise multiple stereocenters. It is aimed to synthesis the enantiopure sulfolipid-I in a short synthesis by utilizing the recent methodology developed by the Aggarwal group involving the reactions of chiral lithiated carbamates with boronic esters. This new strategy is a potentially powerful tool for the iterative asymmetric synthesis of complex molecules in short order."

Call for proposal

FP7-PEOPLE-2011-IEF
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Coordinator

UNIVERSITY OF BRISTOL
EU contribution
€ 209 033,40
Address
BEACON HOUSE QUEENS ROAD
BS8 1QU Bristol
United Kingdom

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Region
South West (England) Gloucestershire, Wiltshire and Bristol/Bath area Bristol, City of
Activity type
Higher or Secondary Education Establishments
Administrative Contact
Audrey Michael (Ms.)
Links
Total cost
No data