Efficient sequential segment coupling using N-alkylcysteine-assisted thioesterification for glycopeptide dendrimer synthesis
Efficient sequential segment coupling using N-alkylcysteine-assisted thioesterification for glycopeptide dendrimer synthesis
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DOI：
10.1021/ol801340m
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发表时间：
2008-08-21
期刊：
影响因子：
5.2
通讯作者：
Nakahara, Yoshiaki
中科院分区：
文献类型：
--
作者：
Ozawa, Chinatsu;Katayama, Hidekazu;Nakahara, Yoshiaki
通过N-烷基半胱氨酸（NAC）辅助的硫代酯化反应实现连续片段偶联，制备了22 kDa的高纯度MUC 1衍生的糖肽树状聚合物。通过Fmoc方法制备具有C-末端NAC的糖肽，并转化为硫酯3-巯基丙酸处理。将硫酯与携带NAC的赖氨酸三聚体缩合，得到四聚体，然后将其转化为硫酯。两个四聚体与乙二胺缩合得到八聚体糖肽树状聚合物。
A highly pure MUC1-derived glycopeptide dendrimer of 22 kDa was prepared by a sequential segment coupling, achieved by an N-alkylcysteine (NAC)-assisted thioesterification. The glycopeptide having C-terminal NAC was prepared by the Fmoc method and converted to the thioester 3-mercaptopgropionic acid treatment. The thioester was condensed with a lysine trimer carrying NAC to afford tetramer, which was then converted to the thioester. Two tetramers were condensed with ethylenediamine to give the octameric glycopeptide dendrimer.