直接合成亚利桑那沙门氏菌O62的o特异性多糖的六糖重复单元。

IF 2.7 4区 生物学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY
Abhijit Rana, Pradip Shit, Anup Kumar Misra
{"title":"直接合成亚利桑那沙门氏菌O62的o特异性多糖的六糖重复单元。","authors":"Abhijit Rana,&nbsp;Pradip Shit,&nbsp;Anup Kumar Misra","doi":"10.1007/s10719-023-10122-x","DOIUrl":null,"url":null,"abstract":"<p><p>A straightforward synthesis of the hexasaccharide repeating unit of the O-specific polysaccharide of Salmonella arizonae O62 was achieved in very good yield applying sequential glycosylation strategy. Successful regioselective glycosylation of the di-hydroxylated L-rhamnose moiety allowed achieving the desired compound in minimum number of synthetic steps. TEMPO catalyzed and [bis(acetoxy)iodo]benzene (BAIB) mediated late stage regioselective oxidation of a primary hydroxyl group into carboxylic acid was achieved in the hexasaccharide derivative. The glycosylation steps were high yielding with high stereochemical outcome. The desired hexasaccharide was obtained in 7% over all yield in fourteen steps starting from suitably functionalized monosaccharide intermediates.</p>","PeriodicalId":12762,"journal":{"name":"Glycoconjugate Journal","volume":null,"pages":null},"PeriodicalIF":2.7000,"publicationDate":"2023-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Straightforward synthesis of the hexasaccharide repeating unit of the O-specific polysaccharide of Salmonella arizonae O62.\",\"authors\":\"Abhijit Rana,&nbsp;Pradip Shit,&nbsp;Anup Kumar Misra\",\"doi\":\"10.1007/s10719-023-10122-x\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>A straightforward synthesis of the hexasaccharide repeating unit of the O-specific polysaccharide of Salmonella arizonae O62 was achieved in very good yield applying sequential glycosylation strategy. Successful regioselective glycosylation of the di-hydroxylated L-rhamnose moiety allowed achieving the desired compound in minimum number of synthetic steps. TEMPO catalyzed and [bis(acetoxy)iodo]benzene (BAIB) mediated late stage regioselective oxidation of a primary hydroxyl group into carboxylic acid was achieved in the hexasaccharide derivative. The glycosylation steps were high yielding with high stereochemical outcome. The desired hexasaccharide was obtained in 7% over all yield in fourteen steps starting from suitably functionalized monosaccharide intermediates.</p>\",\"PeriodicalId\":12762,\"journal\":{\"name\":\"Glycoconjugate Journal\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2023-08-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Glycoconjugate Journal\",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://doi.org/10.1007/s10719-023-10122-x\",\"RegionNum\":4,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Glycoconjugate Journal","FirstCategoryId":"99","ListUrlMain":"https://doi.org/10.1007/s10719-023-10122-x","RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0

摘要

采用顺序糖基化策略,直接合成了亚利桑那沙门氏菌O62的o特异性多糖的六糖重复单元,并获得了很好的产量。二羟基化l -鼠李糖部分的成功区域选择性糖基化可以在最少的合成步骤中获得所需的化合物。在六糖衍生物中实现了TEMPO催化和[双(乙酰氧基)碘]苯(BAIB)介导的伯羟基晚期区域选择性氧化成羧酸。糖基化步骤产率高,立体化学效果好。从合适的单糖中间体开始,经过14步,以7%的产率得到了所需的六糖。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Straightforward synthesis of the hexasaccharide repeating unit of the O-specific polysaccharide of Salmonella arizonae O62.

Straightforward synthesis of the hexasaccharide repeating unit of the O-specific polysaccharide of Salmonella arizonae O62.

A straightforward synthesis of the hexasaccharide repeating unit of the O-specific polysaccharide of Salmonella arizonae O62 was achieved in very good yield applying sequential glycosylation strategy. Successful regioselective glycosylation of the di-hydroxylated L-rhamnose moiety allowed achieving the desired compound in minimum number of synthetic steps. TEMPO catalyzed and [bis(acetoxy)iodo]benzene (BAIB) mediated late stage regioselective oxidation of a primary hydroxyl group into carboxylic acid was achieved in the hexasaccharide derivative. The glycosylation steps were high yielding with high stereochemical outcome. The desired hexasaccharide was obtained in 7% over all yield in fourteen steps starting from suitably functionalized monosaccharide intermediates.

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
Glycoconjugate Journal
Glycoconjugate Journal 生物-生化与分子生物学
CiteScore
6.00
自引率
3.30%
发文量
63
审稿时长
1 months
期刊介绍: Glycoconjugate Journal publishes articles and reviews on all areas concerned with: function, composition, structure, biosynthesis, degradation, interactions, recognition and chemo-enzymatic synthesis of glycoconjugates (glycoproteins, glycolipids, oligosaccharides, polysaccharides and proteoglycans), biochemistry, molecular biology, biotechnology, immunology and cell biology of glycoconjugates, aspects related to disease processes (immunological, inflammatory, arthritic infections, metabolic disorders, malignancy, neurological disorders), structural and functional glycomics, glycoimmunology, glycovaccines, organic synthesis of glycoconjugates and the development of methodologies if biologically relevant, glycosylation changes in disease if focused on either the discovery of a novel disease marker or the improved understanding of some basic pathological mechanism, articles on the effects of toxicological agents (alcohol, tobacco, narcotics, environmental agents) on glycosylation, and the use of glycotherapeutics. Glycoconjugate Journal is the official journal of the International Glycoconjugate Organization, which is responsible for organizing the biennial International Symposia on Glycoconjugates.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信