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使用芳基重氮盐修饰氨基酸。

Modifications of amino acids using arenediazonium salts.

机构信息

Department of Organic Chemistry, Indian Institute of Science, Bangalore, Karnataka 560012, India.

出版信息

Org Biomol Chem. 2019 Sep 28;17(36):8308-8329. doi: 10.1039/c9ob01471c. Epub 2019 Aug 30.

DOI:10.1039/c9ob01471c
PMID:31469151
Abstract

Aryl transfer reactions from arenediazonium salts have started to make their impact in chemical biology with initial forays in the arena of arylative modifications and bio-conjugations of amino acids, peptides and proteins. The unique multimodal reactivity of arenediazonium salts, ranging from thermal or photochemical radical chain reactions, Pd-catalyzed coupling to arylazo-coupling reactions, all under distinct but mild conditions, provides multiple options for side chain modifications of amino acids and peptides and in addition, site-selective protein conjugation and labelling, protein immobilization, azo-bridged macrocyclization, etc. under bio-ambient conditions. The purpose of this review is to highlight these recent advances and to stimulate interest towards broader applications of arenediazonium salts as aryl transfer agents in bioconjugation reactions.

摘要

芳基重氮盐的芳基转移反应已经开始在化学生物学领域产生影响,最初在芳基修饰和氨基酸、肽和蛋白质的生物偶联领域取得了进展。芳基重氮盐具有独特的多模态反应性,包括热或光化学自由基链反应、Pd 催化偶联到芳基偶联反应,所有这些反应都在不同但温和的条件下进行,为氨基酸和肽的侧链修饰以及在生物环境条件下的选择性蛋白质偶联和标记、蛋白质固定化、偶氮桥大环化等提供了多种选择。本文综述的目的是强调这些最新进展,并激发人们对芳基重氮盐作为芳基转移试剂在生物偶联反应中的更广泛应用的兴趣。

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Modifications of amino acids using arenediazonium salts.使用芳基重氮盐修饰氨基酸。
Org Biomol Chem. 2019 Sep 28;17(36):8308-8329. doi: 10.1039/c9ob01471c. Epub 2019 Aug 30.
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Org Biomol Chem. 2013 Jun 14;11(22):3674-91. doi: 10.1039/c3ob40420j.

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