A stereocontrolled synthetic approach to glycopeptides corresponding to the carbohydrate-protein linkage region of cell-surface proteoglycans期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

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A stereocontrolled synthetic approach to glycopeptides corresponding to the carbohydrate-protein linkage region of cell-surface proteoglycans

Authors:	Klaus W Neumann Jun-ichi Tamura and Tomoya Ogawa

Institution:	^a The Institute of Physical and Chemical Research (RIKEN), Wako-shi, Saitama, 351-01, Japan ^b Graduate School of Agriculture and Life Science, University of Tokyo, Yayoi, Bunkyo-ku, Tokyo, 113, Japan

Abstract:	The glycopeptides 1 Full-size image and 2 Full-size image ), carrying the core structure of serine-linked cell-surface proteoglycans were synthesized in a stereocontrolled manner. The carbohydrate key imidate xylosyl donors 3 and glycotetraosyl donors 4 and 5, as well as a tetrapeptide glycosyl acceptor 6, were coupled in the crucial glycosylation step. In these reactions, the application of either trimethylsilyl trifluoromethanesulfonate (TMSOTf) or borontrifluoride etherate (BF₃-Et₂O) as catalysts proved to be highly efficient. The serine linked glycopeptides 34, 36 and 37 thus obtained yielded target compounds 1 and 2 on complete deprotection.

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