Chemoselective and microwave-assisted synthesis of glycopeptoids.
Chemoselective and microwave-assisted synthesis of glycopeptoids.
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糖肽的化学选择性和微波辅助合成。
DOI：
10.1021/ol9021468
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发表时间：
2009
期刊：
影响因子：
5.2
通讯作者：
Carrasco,MichaelR
中科院分区：
文献类型：
--
作者：
Seo,Jiwon;Michaelian,Nairie;Owens,ShawnC;Dashner,ScottT;Wong,AmandaJ;Barron,AnneliseE;Carrasco,MichaelR
N-烷基氨基氧基侧链与未保护的还原糖的化学选择性糖基化已被证明可用于糖肽的合成。在此，我们将N-烷基氨氧基策略扩展到糖肽的合成。AN-甲基氨基氧基亚单体被有效地合成并掺入到类肽中。类肽的糖基化在N-甲基氨基氧基部分进行化学选择性和位点特异性。采用微波辐射可显著提高糖基化程度，缩短反应时间。
The chemoselective glycosylation ofN-alkylaminooxy side chains with unprotected reducing sugars has proven useful for the synthesis of glycopeptides. Herein, we extend theN-alkylaminooxy strategy to the synthesis of glycopeptoids. AN-methylaminooxy submonomer was efficiently synthesized and incorporated into peptoids. Glycosylation of the peptoids proceeded chemoselectively and site-specifically at theN-methylaminooxy moieties. Employing microwave irradiation significantly increased the degree of glycosylation and shortened the reaction times.