Design and Synthesis of Highly Bioactive Sugar-Related Substances

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The following research results have been obtained in this research project.1) Coyolosa which is a natural disaccharide having an unusual structure with a 6,6'-ether- linkage was successfully synthesized. In connection with its anti-diabetic activity, 10 kinds of analogs have been synthesized and it was concluded that the reported structure should be revised. A 6,6'-disaccharide formed from two molecules of mannose might be proposed.2) In the connection of the conversion technique for D-sugar to the corresponding L-sugar with the ring opening and the recyclization, this methodology could be applied to the effective formation of L-aza-sugars and L-thia-sugars.3) Glycosylation using 1-methylenesugar afforded the corresponding α-D-glycoside stereo-selectively. This method could be also applied to synthesize the various types of α-glycosides such as α-oligosaccharides exhibiting a potent biological activity. The penta-saccharide analogue for PI-88 that will be expected as a heparanase inhibitor could be synthesized in a fully protected form.