Chemical trans-glycosylation of bioactive glycolinkage: synthesis of an α-lycotetraosyl cholesterol |
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Authors: | Tsuyoshi Ikeda Ken Yamauchi Kenji Nakanishi Shin-ichi Ito |
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Institution: | a Faculty of Medical and Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan b Department of Biological and Environmental Sciences, Faculty of Agriculture, Yamaguchi University, Yamaguchi 753-8515, Japan |
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Abstract: | The aim of this study was to verify the antitumor role of the β-d-glucopyranosyl-(1→2)-O-β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-d-galactopyranosyl (lycotetraosyl) moiety present in steroidal glycosides from Solanaceous plants. We explored a new chemical trans-glycosylation method using an endoglycosidase called tomatinase that is produced by the tomato pathogen, Fusarium oxysporum f. sp. lycopersici. The lycotetraose, which was prepared by enzymatic hydrolysis of α-tomatine with tomatinase, was converted to glycosyl donors such as trichloroacetimidate, fluoride, and thioglycoside. All obtained glycosyl donors were glycosylated with cholesterol to form α-lycotetraosyl cholesterols in a stereoselective manner. The obtained lycotetraosyl derivatives together with typical natural lycotetraosyl glycosides were examined for their antiproliferative activity. |
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Keywords: | Lycotetraose Tomatinase Glycoconjugate Trans-glycosylation Solanum plant α-Tomatine |
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