1. First total synthesis of trehalose containing tetrasaccharides from Mycobacterium smegmatis
- Author
-
Suvarn S. Kulkarni, Manishkumar A. Chaube, Santanu Jana, and Vikram A. Sarpe
- Subjects
Steric effects ,Glycosylation ,Mycobacterium smegmatis ,Oligosaccharides ,Kansasii ,010402 general chemistry ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,Containing Lipooligosaccharides ,Carbohydrate Conformation ,Antigens ,Physical and Theoretical Chemistry ,biology ,010405 organic chemistry ,Organic Chemistry ,Regioselectivity ,Total synthesis ,Trehalose ,Saccharides ,biology.organism_classification ,Combinatorial chemistry ,0104 chemical sciences ,Benzylidene Acetals ,Gordonae ,Solvent ,chemistry ,Stereoselectivity ,Derivatives ,Analogs - Abstract
Total synthesis of three important trehalose containing tetra-saccharides isolated from Mycobacterium smegmatis is reported for the first time, using regioselective opening of benzylidene acetals and stereoselective glycosylations as key steps. The 1,2-cis stereoselectivity in the glycosylation reactions was achieved using anchimeric assistance from a remote participating group, steric effects and solvent participation. The synthetic strategy can also be utilized for the assembly of structurally related oligosaccharides from M. tuberculosis.
- Published
- 2016