Thiosugars: new perspectives regarding availability and potential biochemical and medicinal applications.
Thiosugars, containing a sulfur atom as heteroatom or a disaccharide linked via a sulfur bridge, possess unique physicochemical properties such as water solubility, which differs from conventional functionalized monosaccharides. The differences in biological activities between thiosugars and their oxygen analogs depend on geometric, conformational, and flexibility differences. They depend also on their electronic differences, the sulfide function being less electronegative and more polarizable than the ethereal moiety. Many functionalized thiosugars occur naturally and are potential targets for the development of carbohydrate-based therapeutics. Among the few new examples of the potential new targets are salacinol and kotalanol, tagetitoxin, thiolactomycin and analogues, mycothiol and analogues, and S-nitrosothiols. These new developments and representative examples of functionalized thiosugar prototypes as potential new targets are presented in this mini review.
Witczak
Zbigniew J
ZJ
Department of Pharmaceutical Sciences, Nesbitt School of Pharmacy, Wilkes University, Wilkes-Barre, PA 18766, USA. witczak@wilkes.edu
Culhane
James M
JM
D002236:Carbohydrate Conformation; D003998:Dicarboxylic Acids / Q000737:chemistry / Q000494:pharmacology*; D009005:Monosaccharides / Q000737:chemistry / Q000494:pharmacology*; D009943:Organophosphorus Compounds / Q000737:chemistry / Q000494:pharmacology*; D013402:Sugar Alcohols / Q000737:chemistry / Q000494:pharmacology*; D013431:Sulfates / Q000737:chemistry / Q000494:pharmacology*; D013865:Thioglycosides / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D013876:Thiophenes / Q000737:chemistry / Q000494:pharmacology
D003998:Dicarboxylic Acids; C114502:Kotalanol; D009005:Monosaccharides; D009943:Organophosphorus Compounds; D013402:Sugar Alcohols; D013431:Sulfates; D013865:Thioglycosides; D013876:Thiophenes; C427963:salacinol; C035068:thiolactomycin; C062221:tagetitoxin