Iminosugars: From Synthesis to Therapeutic Applications

摘要

Iminosugars are one of the most fascinating classes of molecules, inspiring synthetic, mechanistic, and medicinal chemists for more than 40 years. Also called azasugars, iminosugars are cyclic sugars in which the ring oxygen atom is replaced by a nitrogen atom. These polyhydroxylated alkaloids have been found to be potent inhibitors of glycosidases, enzymes which cleave glycosidic bonds. The iminosugar with a proto-nated nitrogen atom is believed to be a transition-state mimic of the developing pyranosyl or furanosyl cationic intermediate formed during the enzyme-catalyzed anomeric bond cleavage, where the relative inhibitory activity of each iminosugar depends upon its stereochemical match to the carbohydrate substrate.