立体选择性半乳糖丙酮酰化合成细菌荚膜多糖的结构分析。

IF 2.1 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2025-08-21 eCollection Date: 2025-01-01 DOI:10.3762/bjoc.21.131

Tsun-Yi Chiang, Mei-Huei Lin, Chun-Wei Chang, Jinq-Chyi Lee, Cheng-Chung Wang

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引用次数: 0

摘要

丙酮酸酮是一种生物必需基团，在生物体内作为代谢途径的中间体，是合成各种生物必需分子的关键前体。然而，丙酮酸酮的R/S立体化学很难通过化学方法进行控制。本研究谨慎构建了连接半乳糖4位和6位的酸不稳定丙酮酸酮，并成功获得了r构型产物的x射线分析结果。随后，将该化合物用于两性离子多糖A1 （PS A1）前体的合成，并通过核磁共振和x射线对其进行了清晰的结构解析。

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Structural analysis of stereoselective galactose pyruvylation toward the synthesis of bacterial capsular polysaccharides.

Pyruvate ketal is a biologically essential moiety due to its key role as an intermediate in metabolic pathways, serving as a key precursor for the synthesis of various essential biomolecules in organisms. However, the R/S stereochemistry of pyruvate ketal is difficult to control through chemical methods. In this study, the acid-labile pyruvate ketal linked to the 4- and 6-positions of galactose was cautiously constructed, and the X-ray analysis of the R-configured product was successfully obtained. Subsequently, the compound was used for the synthesis of zwitterionic polysaccharide A1 (PS A1) precursor, and a clear structural elucidation was applied by using nuclear magnetic resonance and X-ray.

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来源期刊

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

期刊介绍： The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.