New glycomimetics: Anomeric sulfonates, sulfenamides, and sulfonamides

CARB 79

Ben Amorelli, amorelli@rutchem.rutgers.edu and Spencer Knapp. Department of Chemistry & Chemical Biology, Rutgers The State University of New Jersey, 610 Taylor Road, Piscataway, NJ 08854-8087
The synthesis of a variety of new 1-thio-D-glucopyranoses oxidized at the sulfur atom is described, including seven 1-C-sulfonic acids, three sulfonate esters, three sulfinate esters, an S,S'-diglycosyl thiolsulfonate and thiolsulfinate, four S-glycosyl sulfenamides, an S-glycosyl sulfinamide, and two S-glycosyl sulfonamides. These compounds possess unusual anomeric functionality that might be resistant or even inhibitory to normal enzymatic carbohydrate processing, and therefore they may be of future use in studies of enzyme inhibition, structure, mechanism, and function.