New glycomimetics: anomeric sulfonates, sulfenamides, and sulfonamides.
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.
Knapp
Spencer
S
Department of Chemistry & Chemical Biology, Rutgers--State University of New Jersey, 610 Taylor Road, Piscataway, New Jersey 08854, USA. knapp@rutchem.rutgers.edu
Darout
Etzer
E
Amorelli
Benjamin
B
D002241:Carbohydrates / Q000037:antagonists & inhibitors / Q000096:biosynthesis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D018716:Molecular Mimicry; D013416:Sulfamerazine / Q000138:chemical synthesis; D013449:Sulfonamides / Q000138:chemical synthesis; D013451:Sulfonic Acids / Q000138:chemical synthesis; D013457:Sulfur Compounds / Q000138:chemical synthesis*
D002241:Carbohydrates; D004791:Enzyme Inhibitors; D006027:Glycosides; D013449:Sulfonamides; D013451:Sulfonic Acids; D013457:Sulfur Compounds; C471392:sulfenamide; D013416:Sulfamerazine