1. Expeditious Synthesis of Mycobacterium tuberculosis Sulfolipids SL-1 and Ac(2)SGL Analogues
- Author
-
Suvarn S. Kulkarni and Vikram A. Sarpe
- Subjects
Molecular Structure ,biology ,Virulence Factors ,Chemistry ,Stereochemistry ,Sulfates ,Organic Chemistry ,Late stage ,Regioselectivity ,Trehalose ,Sulfoglycolipids ,Mycobacterium tuberculosis ,biology.organism_classification ,Biochemistry ,Combinatorial chemistry ,Strain H37rv ,Sulfation ,Bacterial Vaccines ,Glycolipids ,Physical and Theoretical Chemistry ,Antigens ,Acyl Chains - Abstract
M. tuberculosis sulfoglycolipids SL-1 and Ac(2)SGL are highly immunogenic and potential vaccine candidates. A short and efficient methodology is reported for the synthesis of SL-1 and Ac(2)SGL analogues via regioselective functionalization of alpha,alpha-D-trehalose employing a highly regioselective late stage sulfation, as a key step. The SL-1 analogues 3a and 4 were obtained in 10 and 9 steps in 13.4% and 23.9% overall yields, respectively. The Ac(2)SGL analogue 5 was synthesized in 5 steps in 18.4% yield.
- Published
- 2014