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首页> 外文期刊>Chemistry: A European journal >A double regio- and stereoselective glycosylation strategy for the synthesis of N-glycans
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A double regio- and stereoselective glycosylation strategy for the synthesis of N-glycans

机译：N-聚糖合成的双重区域和立体选择性糖基化策略

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摘要

A building block approach for biantennary N-linked oligosaccharides from glycoproteins (N-glycans) has been developed. Starting from a core trisaccharide (P-mannosyl chitobiose) containing a benzylidene-protected beta-mannoside, the attachment of the disaccharide building blocks for the antennae can be performed in a double regio- and stereoselective manner. A short synthesis of a GlcNPht beta 1,2Man donor was developed. The benzylidene acetal moiety, as a minimal protection of the P-mannoside, allows selective alpha-glycosylation at OH-3 of the 2,3-diol with GlcN beta 1,2Man trichloroacetimidate donors. Subsequent debenzylidenation leads to a 4,6-diol, which can be selectively extended at OH-6. Overreaction at OH-4 was generally low when phthalimido-protected donors were used. This general strategy represents a modular synthesis of N-glycans and their glycoconjugates.
机译：已经开发了一种用于糖蛋白（N-聚糖）的双天线N-连接寡糖的构建方法。从包含亚苄基保护的β-甘露糖苷的核心三糖（P-甘露糖基壳二糖）开始，用于触角的二糖结构单元的连接可以以区域和立体选择性的双重方式进行。开发了GlcNPht beta 1,2Man供体的简短合成。作为对P-甘露糖苷的最小保护，亚苄基乙缩醛部分允许使用GlcNβ1,2Man三氯乙酰亚氨酸酯供体在2,3-二醇的OH-3处进行选择性α-糖基化。随后的脱苄基作用产生4，6-二醇，其可以在OH-6处选择性地延伸。当使用邻苯二甲酰亚胺保护的供体时，OH-4的过度反应通常较低。该一般策略代表了N-聚糖及其糖缀合物的模块化合成。

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