Synthesis of beta-analogues of C-mannosyltryptophan, a novel C-glycosylamino acid found in proteins.
Synthesis of beta-analogues of C-mannosyltryptophan, a novel C-glycosylamino acid found in proteins.
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DOI：
10.1039/b516282c
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发表时间：
2006-03
影响因子：
3.2
通讯作者：
T. Nishikawa;Y. Koide;A. Kanakubo;H. Yoshimura;M. Isobe
中科院分区：
文献类型：
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作者：
T. Nishikawa;Y. Koide;A. Kanakubo;H. Yoshimura;M. Isobe
α-C-甘露糖基色氨酸（alpha-C-Man-Trp）是色氨酸的一种新型翻译后修饰，它存在于一些重要的糖蛋白中。为了分析α-C-Man-Trp的生物学功能，我们开发了一种高效的合成策略，从相应的六吡喃糖苷衍生物与锡乙炔的α-C-糖苷化反应开始，合成了α-C-Man-Trp及其葡萄糖和半乳糖类似物。根据这些合成路线，我们在这里描述了从相应的β-C-糖基乙炔合成C-Man-Trp的β-端基异构体及其葡萄糖和半乳糖类似物。在这项研究中，我们开发了一种高度立体控制的合成β-C-甘露糖基乙炔，这是合成β-C-Man-Trp所需的，而以前的方法得到了C-甘露糖基乙炔的异头混合物。用HPLC对合成的C-Man-Trp及其类似物进行了分析。
alpha-C-Mannosyltryptophan (alpha-C-Man-Trp) has been found to be a novel post-translational modification of tryptophan found from some biologically important glycoproteins. In order to analyze the biological functions of alpha-C-Man-Trp, we have developed an efficient synthetic strategy for alpha-C-Man-Trp and its glucose and galactose analogues, starting from alpha-C-glycosidation of the corresponding hexapyranoside derivatives with tinacetylene. According to the synthetic routes, we describe here syntheses of beta-anomers of C-Man-Trp, and its glucose and galactose analogues from the corresponding beta-C-glycosylacetylenes. During this study, we have developed a highly stereocontrolled synthesis of beta-C-mannosylacetylene that is required for the synthesis of beta-C-Man-Trp, while the precedented method gave an anomeric mixture of the C-mannosylacetylene. The synthetic C-Man-Trp and its analogues were analyzed by HPLC.