Department of Bioengineering, Stanford University, 318 Campus Drive, Stanford, California 94305-5440, USA.
Org Lett. 2009 Nov 19;11(22):5210-3. doi: 10.1021/ol9021468.
The chemoselective glycosylation of N-alkylaminooxy side chains with unprotected reducing sugars has proven useful for the synthesis of glycopeptides. Herein, we extend the N-alkylaminooxy strategy to the synthesis of glycopeptoids. A N-methylaminooxy submonomer was efficiently synthesized and incorporated into peptoids. Glycosylation of the peptoids proceeded chemoselectively and site-specifically at the N-methylaminooxy moieties. Employing microwave irradiation significantly increased the degree of glycosylation and shortened the reaction times.
N-烷氨基氧基侧链与未保护还原糖的化学选择性糖基化已被证明对糖肽的合成有用。在此，我们将 N-烷氨基氧基策略扩展到糖肽拟肽的合成中。高效合成了 N-甲氨基氧基亚单体制备并将其掺入到肽拟肽中。糖基化反应在 N-甲氨基氧基部位选择性和特异性地进行。微波辐射的使用显著提高了糖基化程度并缩短了反应时间。
