一种立体控制的合成方法，用于合成与细胞表面蛋白聚糖的碳水化合物-蛋白质连接区域相对应的糖肽。
A stereocontrolled synthetic approach to glycopeptides corresponding to the carbohydrate-protein linkage region of cell-surface proteoglycans.
作者信息
Neumann K W, Tamura J, Ogawa T
机构信息
Institute of Physical and Chemical Research (RIKEN), Saitama, Japan.
出版信息
Bioorg Med Chem. 1995 Dec;3(12):1637-50. doi: 10.1016/0968-0896(95)00151-4.
The glycopeptides 1 (Gly[O-beta-D-Xylp)-L-Ser-Gly-L-Glu) and 2 (Gly[O-[beta-D-GlcpA-(1-->3)-beta-D-Galp-(1-->3)-beta-D-Galp]-(1-- >4) -beta-D-Xylp)-L-Ser-Gly-L-Glu), 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.
以立体控制的方式合成了带有丝氨酸连接的细胞表面蛋白聚糖核心结构的糖肽1（甘氨酸[O-β-D-木糖基）-L-丝氨酸-甘氨酸-L-谷氨酸）和2（甘氨酸[O-[β-D-葡萄糖醛酸-(1→3)-β-D-半乳糖-(1→3)-β-D-半乳糖]-(1→4)-β-D-木糖基)-L-丝氨酸-甘氨酸-L-谷氨酸）。在关键的糖基化步骤中，将碳水化合物关键亚胺酸木糖基供体3、糖四糖基供体4和5以及四肽糖基受体6进行了偶联。在这些反应中，使用三甲基甲硅烷基三氟甲磺酸酯（TMSOTf）或三氟化硼乙醚（BF3-Et2O）作为催化剂被证明是非常有效的。由此得到的丝氨酸连接的糖肽34、36和37在完全脱保护后得到目标化合物1和2。
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