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Synthesis of the tetrasaccharide repeating unit of the O-glycan from the polar flagellum flagellin of Azospirillum brasilense Sp7

机译:从巴西细螺旋体Sp7的极鞭毛鞭毛蛋白合成O-聚糖的四糖重复单元

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Chemical synthesis of the tetrasaccharide repeating unit of the O-glycan from the polar flagellum flagellin of Azospirillum brasilense Sp7 in the form of its p-methoxyphenyl glycoside is reported. The required glycosidic linkages have been accomplished by activation of thioglycosides with N-iodosuccinimide in the presence of H2SO4-silica. H2SO4-silica was found to be an effective alternative to the classical acid promoters like TfOH or TMSOTf and it can lead to the formation of both 1,2-cis and 1,2-trans glycosidic linkages depending on the protecting group manipulation and control of the reaction condition. (C) 2014 Elsevier Ltd. All rights reserved.
机译:据报道,从巴西细螺旋体Sp7的极性鞭毛鞭毛蛋白以其对甲氧基苯基糖苷的形式化学合成了O-聚糖的四糖重复单元。通过在H 2 SO 4-二氧化硅存在下用N-碘代琥珀酰亚胺活化硫糖苷来完成所需的糖苷键。发现H2SO4-二氧化硅是经典的酸促进剂(如TfOH或TMSOTf)的有效替代物,它可以导致1,2-顺式和1,2-反式糖苷键的形成,具体取决于保护基的操纵和控制。反应条件。 (C)2014 Elsevier Ltd.保留所有权利。

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