New glycomimetics: Anomeric sulfonates, sulfenamides, and sulfonamides

作者:Knapp S*; Darout E; Amorelli B
来源:Journal of Organic Chemistry, 2006, 71(4): 1380-1389.
DOI:10.1021/jo0520386

摘要

The synthesis of a variety of new 1-thio-D-glucopyranose derivatives 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.

  • 出版日期2006-2-17