Chemo- and stereoselective glycosylation of hydroxylamino derivatives: A versatile approach to glycoconjugates
Chemo- and stereoselective glycosylation of hydroxylamino derivatives: A versatile approach to glycoconjugates
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DOI：
10.1016/s0040-4020(98)00763-7
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发表时间：
1998-10-01
期刊：
影响因子：
2.1
通讯作者：
Mutter, M
中科院分区：
文献类型：
--
作者：
Peri, F;Dumy, P;Mutter, M
描述了一种用于未保护的寡糖与任何含有N，O-二取代羟胺基团的底物的立体选择性偶联的通用方法。寡糖还原单元的环状性质得以保留，底物通过氨基（N[OR 2]-）或氨氧基（N[R-1]-O-）键以高非对映选择性糖基化。由于二取代羟胺对糖还原末端的独特高化学反应性和特异性，在水溶液中进行反应既不需要保护基团也不需要活化方法。这种新型的糖基化反应的特点和范围的例子为模型糖肽的化学选择性合成。(C)1998爱思唯尔科技有限公司。保留所有权利。
A general method for the stereoselective coupling of unprotected oligosaccharides with any substrate containing a N,O-disubstituted hydroxylamine group is described. The cyclic nature of the oligosaccharide reducing unit is preserved and the substrate glycosylated with high diastereoselectivity to sugar through an amino (N[OR2]-) or an aminoxy (N[R-1]-O-) linkage. Due to the uniquely high chemical reactivity and specificity of disubstituted hydroxylamine toward the sugar reducing end, neither protecting groups nor activation methods are required to perform the reaction in aqueous solution. The characteristic features and the scope of this new type of glycosylation reaction are exemplified for the chemoselective synthesis of model glycopeptides. (C) 1998 Elsevier Science Ltd. All rights reserved.