Cyclic thiosugar derivatives from levoglucosenone as precursors in glycosylation chemistry

COMBA, M. B.; MANGIONE, M. I; SUÁREZ, A. G.; SAROTTI, A. M.; SPANEVELLO, R. A.

Villa Gral Belgrano

Simposio; GlycoAR 2016; 2016

Thiosugarspossess characteristic biological and physicochemical properties which differfrom their oxygenated counterparts. Many functionalized thiosugars occurnaturally and have shown to be useful tools for probing carbohydrate-proteininteractions within enzymes systems and have potential as therapeutics. Amongthe families of synthetic thiosugars with biological activities, it can bementioned that glycosyl S-nitrosothiols act as nitric oxide donors, S-tritylglycosides as chemotheraphy agent, 5-thiosugars as enzyme inhibitors,3-thiosugars as neuraminidase inhibitors, thio-linked analogs of Lewis A and Bas antigens, thioanalogs of Amiloprilose as useful immunomodulators fortreating autoimmnune disorders. Recently, thioglycosides derived from acceptorsugars as 3-thiogalactopyrano-, 4-thioglucopyrano- and 4-thiomannopyranosideshave been developed as b-galactosidaseinhibitors. The synthesis of thioglycosides requires the appropriatepreparation of a thiosugar as glycosyl acceptor or donor derivative. In thepresent work we describe the synthesis of two sugar derivatives fromlevoglucosenone containing sulfur functionalities: a cyclic system1,3-oxatiolan-2-thione as glycosyl donor and a 3-thiommanoside as glycosylacceptor. Both sulfur-containing monosaccharides are properly functionalized withinteresting synthetic behaviors which turn them into versatile building blocksfor the development of carbohydrate-based therapeutics.