Chemistry and Biology of Iminosugar Di- and Oligosaccharides

Biosynthetic Pathways to Glycosidase Inhibitors

“…for pyrrolidines, [34,35] piperidines, [36,37] bicyclic compounds such as indolizidines [38] and pyrrolizidines [39,40] and imino disaccharides. [41,42] However, only a little is known about biosynthetic routes towards that sort of compounds. It can be expected that the knowledge of the biosynthetic Post-print de Current Chemical Biology 2014, 8, 10-16 pathways can be used to manipulate the metabolite pattern of involved microorganisms, directing the fermentation process to produce desired metabolites.…”

Stereoselective Access to the β‐D‐N‐Acetylhexosaminyl‐(1→4)‐1‐deoxy‐D‐nojirimycin Disaccharide Series Avoiding the Glycosylation Reaction

“…This new binding pattern with the enzyme could give higher enzymatic selectivity. Synthetic efforts have been directed towards the synthesis of di‐ and oligosaccharide iminosugars,8 and in some cases the larger structures proved to be better inhibitors than the parent monosaccharide compounds 9. Although several synthetic approaches have been developed during the past decades to prepare monosaccharide iminosugars,2a,10 including condensation reactions, amination reactions, organometallic catalysis, pericyclic reactions, and addition reactions, the typical approach8 that is used to prepare di‐ and oligosaccharide iminosugars is to perform a glycosylation reaction between a suitably protected glycosyl donor and a selectively deprotected iminosugar acceptor.…”