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通过氰氧基自由基介导的聚合反应从游离聚糖直接合成α-聚糖聚合物

Straightforward Synthesis of -Glycan Polymers from Free Glycans via Cyanoxyl Free Radical-Mediated Polymerization.

作者信息

Tang Jinshan, Ozhegov Evgeny, Liu Yang, Wang Dan, Yao Xinsheng, Sun Xue-Long

机构信息

Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, West 601, Huangpu Avenue, Guangzhou, People's Republic of China.

Department of Chemistry, Chemical and Biomedical Engineering and Center for Gene Regulation in Health and Disease (GRHD), Cleveland State University, 2121 Euclid Avenue, Cleveland, Ohio 44115, United States.

出版信息

ACS Macro Lett. 2017 Feb 21;6(2):107-111. doi: 10.1021/acsmacrolett.6b00928. Epub 2017 Jan 18.

Abstract

We report a straightforward synthesis of -glycan polymers from free glycans via glycosylamine intermediates followed by acrylation and polymerization via cyanoxyl-mediated free radical polymerization (CMFRP) in one-pot fashion. No protection and deprotection were used in either glycomonomer or glycopolymer synthesis. A typical synthetic procedure for -glycan polymers from free monosaccharide and disaccharide, Glc, Gal, Man, GlcNAc, and Lac, was demonstrated. In addition, enzymatic sialylation of the Lac-containing -glycan polymers and their anti-influenza virus hemagglutination activities were investigated.

摘要

我们报道了一种通过糖基胺中间体从游离聚糖直接合成聚糖聚合物的方法,随后通过氰氧基介导的自由基聚合(CMFRP)以一锅法进行丙烯酸化和聚合。在聚糖单体或聚糖聚合物合成中均未使用保护和脱保护步骤。展示了从游离单糖和二糖(葡萄糖、半乳糖、甘露糖、N-乙酰葡糖胺和乳糖)合成聚糖聚合物的典型合成步骤。此外,还研究了含乳糖的聚糖聚合物的酶促唾液酸化及其抗流感病毒血凝活性。

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