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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."

Field of science

  • /natural sciences/biological sciences/biochemistry/biomolecules/carbohydrates
  • /medical and health sciences/clinical medicine/pneumology/tuberculosis
  • /natural sciences/biological sciences/biochemistry/biomolecules/lipids

Call for proposal

FP7-PEOPLE-2011-IEF
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Funding Scheme

MC-IEF - Intra-European Fellowships (IEF)

Coordinator

UNIVERSITY OF BRISTOL
Address
Beacon House Queens Road
BS8 1QU Bristol
United Kingdom
Activity type
Higher or Secondary Education Establishments
EU contribution
€ 209 033,40
Administrative Contact
Audrey Michael (Ms.)