Boron enabled bioconjugation chemistries

IF 40.4 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Chemical Society Reviews Pub Date : 2024-10-30 DOI:10.1039/d4cs00750f
Mengmeng Zheng, Lingchao Kong, Jianmin Gao
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Abstract

Novel bioconjugation reactions have been heavily pursued for the past two decades. A myriad of conjugation reactions have been developed for labeling molecules of interest in their native context as well as for constructing multifunctional molecular entities or stimuli-responsive materials. A growing cluster of bioconjugation reactions were realized by tapping into the unique properties of boron. As a rare element in human biology, boronic acids and esters exhibit remarkable biocompatibility. A number of organoboron reagents have been evaluated for bioconjugation, targeting the reactivity of either native biomolecules or those incorporating bioorthogonal functional groups. Owing to the dynamic nature of B–O and B–N bond formation, a significant portion of the boron-enabled bioconjugations exhibit rapid reversibility and accordingly have found applications in the development of reversible covalent inhibitors. On the other hand, stable bioconjugations have been developed that display fast kinetics and significantly expand the repertoire of bioorthogonal chemistry. This contribution presents a summary and comparative analysis of the recently developed boron-mediated bioconjugations. Importantly, this article seeks to provide an in-depth discussion of the thermodynamic and kinetic profiles of these boron-enabled bioconjugations, which reveals structure–reactivity relationships and provides guidelines for bioapplications.

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支持硼的生物共轭化学物质
过去二十年来,人们一直在大力研究新型生物共轭反应。人们开发了无数种共轭反应,用于标记感兴趣分子的原生环境,以及构建多功能分子实体或刺激响应材料。通过利用硼的独特性质,越来越多的生物共轭反应得以实现。作为人类生物学中的稀有元素,硼酸和硼酸酯具有显著的生物相容性。针对原生生物大分子或含有生物正交官能团的生物大分子的反应活性,对许多有机硼试剂进行了生物共轭评估。由于 B-O 和 B-N 键形成的动态性质,相当一部分硼促成的生物共轭表现出快速的可逆性,因此被应用于可逆共价抑制剂的开发。另一方面,已开发出的稳定生物共轭物显示出快速的动力学特性,极大地扩展了生物正交化学的范围。本文对最近开发的硼介导的生物共轭物进行了总结和比较分析。重要的是,本文试图深入探讨这些硼赋能生物共轭的热力学和动力学特征,从而揭示结构-反应关系,并为生物应用提供指导。
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来源期刊
Chemical Society Reviews
Chemical Society Reviews 化学-化学综合
CiteScore
80.80
自引率
1.10%
发文量
345
审稿时长
6.0 months
期刊介绍: Chemical Society Reviews is published by: Royal Society of Chemistry. Focus: Review articles on topics of current interest in chemistry; Predecessors: Quarterly Reviews, Chemical Society (1947–1971); Current title: Since 1971; Impact factor: 60.615 (2021); Themed issues: Occasional themed issues on new and emerging areas of research in the chemical sciences
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