Dimethoxy Triazine Glycosides as New Glycosyl Donors for Chemo-enzymatic Synthesis of Oligosaccharides

Abstract

Various 4-(4,6-dimethoxy-1,3,5-triazin-2-yl) glycosides (DMT-glycosides) have been synthesized from the corresponding free sugars in water by using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methyl-morpholinium chloride (DMT-MM) as a dehydrative condensing agent. The resulting DMT-glycosides were found to be recognized as substrates for glycosyl hydrolases and could be utilized as novel glycosyl donors for chemo-enzymatic glycosylations. DMT-glycosides will be efficient and general glycosyl donors for glycosidase-catalyzed transglycosylation reaction in the field of carbohydrate chemistry.