Sugar-assisted glycopeptide ligation
Sugar-assisted glycopeptide ligation
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DOI：
10.1021/ja061165w
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发表时间：
2006-05-03
影响因子：
15
通讯作者：
Wong, CH
中科院分区：
文献类型：
--
作者：
Brik, A;Yang, YY;Wong, CH
从容易获得的材料中化学合成糖肽和糖蛋白为结构和功能研究提供了一条有吸引力的均质产品路线。基于天然化学连接的糖肽和糖蛋白的化学合成代表了用于合成天然糖肽结构的有用方法之一。在这里，我们描述了一种方法，允许从无半胱氨酸的肽合成糖肽。该方法利用肽硫酯和糖肽，其中糖部分在C-2位用硫醇柄修饰。在连接反应完成后，硫醇柄可以用H2/金属还原成乙酰胺部分，提供未修饰的糖肽。总之，这一系列反应在糖肽和糖蛋白合成中显示出有吸引力的潜力。
The chemical synthesis of glycopeptides and glycoproteins from readily available materials presents an attractive route to homogeneous products for structural and functional studies. Chemical synthesis of glycopeptides and glycoproteins based on native chemical ligation represents one of the useful methods for the synthesis of natural glycopeptide structures. Here we describe a method that allows for the synthesis of glycopeptides from cysteine-free peptides. This method utilizes a peptide thioester and a glycopeptide in which the sugar moiety is modified with a thiol handle at the C-2 position. Upon completion of the ligation reaction, the thiol handle can be reduced with H2/metal to the acetamide moiety, furnishing the unmodified glycopeptides. Together, this sequence of reactions displays an attractive potential in glycopeptides and glycoproteins synthesis.