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

IF 1.2 4区化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Journal of Carbohydrate Chemistry 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

{"title":"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","authors":"Hongli Hou , Guangzong Tian , Junjie Fu , Chunjun Qin , Guodong Chen , Xiaopeng Zou , Jing Hu , Jian Yin","doi":"10.1080/07328303.2022.2055049","DOIUrl":null,"url":null,"abstract":"<div><p>The highly stereoselective synthesis of complex carbohydrates containing 1,2-<em>cis</em>-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-<em>cis</em>-D-quinovosamine linkages. The strategy is applied to the preparation of natural disaccharide present on the surface of <em>Pseudomonas aeruginosa</em> 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.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 2","pages":"Pages 155-180"},"PeriodicalIF":1.2000,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Highly stereoselective construction of 1,2-cis-D-quinovosamine glycosides for the synthesis of Pseudomonas aeruginosa O-antigen disaccharide\",\"authors\":\"Hongli Hou , Guangzong Tian , Junjie Fu , Chunjun Qin , Guodong Chen , Xiaopeng Zou , Jing Hu , Jian Yin\",\"doi\":\"10.1080/07328303.2022.2055049\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>The highly stereoselective synthesis of complex carbohydrates containing 1,2-<em>cis</em>-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-<em>cis</em>-D-quinovosamine linkages. The strategy is applied to the preparation of natural disaccharide present on the surface of <em>Pseudomonas aeruginosa</em> 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.</p></div>\",\"PeriodicalId\":15311,\"journal\":{\"name\":\"Journal of Carbohydrate Chemistry\",\"volume\":\"41 2\",\"pages\":\"Pages 155-180\"},\"PeriodicalIF\":1.2000,\"publicationDate\":\"2022-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Carbohydrate Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S0732830322000325\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Carbohydrate Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S0732830322000325","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}

引用次数: 0

摘要

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。

查看原文本刊更多论文

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

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.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Journal of Carbohydrate Chemistry 化学-生化与分子生物学

CiteScore

2.10

自引率

0.00%

发文量

审稿时长

1 months

期刊介绍： The Journal of Carbohydrate Chemistry serves as an international forum for research advances involving the chemistry and biology of carbohydrates. The following aspects are considered to fall within the scope of this journal: -novel synthetic methods involving carbohydrates, oligosaccharides, and glycoconjugates- the use of chemical methods to address aspects of glycobiology- spectroscopic and crystallographic structure studies of carbohydrates- computational and molecular modeling studies- physicochemical studies involving carbohydrates and the chemistry and biochemistry of carbohydrate polymers.