21 自動合成を指向した生理活性糖鎖のライブラリー構築 : ファイトアレキシンエリシター活性を有する糖質の合成と構造活性相関(口頭発表の部)

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Oligosaccharides play a lot of important roles in biological processes and in pathology. While the automated synthesis of peptides and oligonucleotides was established decades ago, there have not been a general method for the synthesis of complex oligosaccharides. Recently the development of a broadly applicable synthetic strategy has been desired in this field. Here we wish to report the two efficient and practical strategies based on a one-pot sequential glycosidation and selective deprotection followed by glycosylation toward the automated synthesis of a oligosaccharide library. In the synthesis of heptasaccharide 3 having elicitor activity in soybean, we achieved a onepot 6-step glycosidation using a combination of different leaving groups, i.e., bromide (-Br), ethylthio group (-SEt), phenylthio group (-SPh), and fluoride (-F), with selective activators, AgOTf, MeOTf, DMTST, and HfCp_2(OTf)_2, respectively and differences of the reactivity of hydroxy groups of glycosyl acceptors. This method was applied to synthesize a library of tetra-, penta-, heptasaccharides using a manual synthesizer. For a study of the structure-activity relationship of elicitor active oligosaccharide in rice cell we demonstrated the synthesis of the oligosaccharide library having β(1→6) linkage at the various positions on β(1→3) tetrasaccharide backborn. Selective deprotection of three protecting groups (AOC, Lev, and Fmoc) of tetrasaccharide 4 was sequentially achieved to afford respective three mono-ols, three diols, and one triol, independently. Glycosylation of all glycosyl acceptors provided the corresponding oligosaccharides, respectively. These procedures were achieved on an automated synthesizer and by parallel column chromatography.
天然有機化合物討論会の論文
2000-10-01

21 自動合成を指向した生理活性糖鎖のライブラリー構築 : ファイトアレキシンエリシター活性を有する糖質の合成と構造活性相関(口頭発表の部)

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