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
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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.

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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.
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