Efficient stereoselective synthesis of γ-N-glycosyl asparagines by N-glycosylation of primary amide groups
Efficient stereoselective synthesis of γ-N-glycosyl asparagines by N-glycosylation of primary amide groups
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DOI：
10.1021/ja0450298
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发表时间：
2005-02-16
影响因子：
15
通讯作者：
Takahashi, T
中科院分区：
文献类型：
--
作者：
Tanaka, H;Iwata, Y;Takahashi, T
介绍了用含天冬酰胺肽的n -糖基化法高效、简便地合成n -糖苷的方法。在硝化甲烷中，在一定催化量的TMSOTf存在下，伯胺与糖基n -苯三氟酰酸酯的糖基化反应顺利进行，以优异的收率提供相应的n -糖基氨基酸。这种偶联方法适用于各种糖基给体与氨基酸和多肽的偶联。
The efficient and elegant synthesis ofN-glycosides by N-glycosylation of asparagine-containing peptides is described. Glycosylation of primary amides with glycosylN-phenyltrifluoroimidates in the presence of a catalytic amount of TMSOTf in nitromethane smoothly proceeded to provide the correspondingN-glycosyl amino acids in excellent yields. This coupling method was adaptable to the coupling of various glycosyl donors with amino acids and peptides.