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卤代糖作为糖基自由基前体在可见光催化糖基化反应中的应用简述

A brief account of the application of glycosyl halide as glycosyl radical precursor towards glycosylation through visible light catalysis.

作者信息

Das Ramanand, Haldar Rahul, Zargar Irshad Ahmad, Bappa S K, Kundu Taraknath, Mukherjee Debaraj

机构信息

National Institute of Technology Sikkim, Ravangla, Namchi, Sikkim, 737139, India; Bose Institute, Bidhan Nagar, Kolkata, 700091, India.

Bose Institute, Bidhan Nagar, Kolkata, 700091, India.

出版信息

Carbohydr Res. 2025 Aug;554:109537. doi: 10.1016/j.carres.2025.109537. Epub 2025 May 17.

Abstract

Glycosylation is potentially one of the most important reactions in glycochemistry, where precise control over the anomeric selectivity is crucial for synthesizing biologically relevant glycoconjugates. Over the last two decades, the advent of visible light chemistry for the generation of glycosyl radicals and its application in the synthesis of glycosides has revolutionized the impact on the stereoselectivity of glycosylation. The visible light-driven radical-based reactions offer exceptional functional group tolerance, operate under mild reaction conditions, and have emerged as a powerful tool for synthesizing potent glycosyl compounds, which include aryl/alkyl glycosides, 2-deoxy sugar, glycosylamino acid, glycosylpeptides, and other glyco-conjugates. In this review article, a brief account of the evolution of glycosyl radical chemistry, with a focus on the visible light-mediated activation of glycosyl halides and its transformative impact on glycoside synthesis, has been discussed.

摘要

糖基化可能是糖化学中最重要的反应之一,其中对异头选择性的精确控制对于合成具有生物学意义的糖缀合物至关重要。在过去的二十年中,用于生成糖基自由基的可见光化学的出现及其在糖苷合成中的应用彻底改变了对糖基化立体选择性的影响。可见光驱动的基于自由基的反应具有出色的官能团耐受性,在温和的反应条件下进行,并且已成为合成强效糖基化合物的有力工具,这些化合物包括芳基/烷基糖苷、2-脱氧糖、糖基氨基酸、糖基肽和其他糖缀合物。在这篇综述文章中,简要介绍了糖基自由基化学的发展,重点讨论了可见光介导的糖基卤化物活化及其对糖苷合成的变革性影响。

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