Highly stereoselective construction of 1,2-cis-D-quinovosamine glycosides for the synthesis of Pseudomonas aeruginosa O-antigen disaccharide

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Accounts of Chemical Research Pub Date : 2022-01-01 DOI:10.1080/07328303.2022.2055049

Hongli Hou , Guangzong Tian , Junjie Fu , Chunjun Qin , Guodong Chen , Xiaopeng Zou , Jing Hu , Jian Yin

引用次数: 0

Abstract

The highly stereoselective synthesis of complex carbohydrates containing 1,2-cis-quinovosamine is an on-going challenge. Here, we report a synergistic strategy of merging reagent modulation and acyl remote participation for highly stereoselective construction of 1,2-cis-D-quinovosamine linkages. The strategy is applied to the preparation of natural disaccharide present on the surface of Pseudomonas aeruginosa bacteria. The resulting disaccharide can be covalently bound to microarray surface or carrier via the aminopentyl linker at the reducing end, allowing for exploring its antigenic and immunogenic properties.

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1,2-顺式- d -喹啉氨基糖苷的高立体选择性构建合成铜绿假单胞菌o抗原双糖

高度立体选择性合成含有1,2-顺式-喹诺糖胺的复合碳水化合物是一个持续的挑战。在这里，我们报道了一种融合试剂调制和酰基远程参与的协同策略，用于高度立体选择性的1,2-顺式- d -喹诺胺键的构建。该方法应用于铜绿假单胞菌表面天然双糖的制备。所得到的双糖可以通过还原端的氨基戊基连接物与微阵列表面或载体共价结合，从而可以探索其抗原和免疫原性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.