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Hypersensitive azobenzenes: facile synthesis of clickable and cleavable azo linkers with tunable and high reducibility.
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2020-01-06 , DOI: 10.1039/c9ob02515d Taejun Eom 1 , Anzar Khan
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2020-01-06 , DOI: 10.1039/c9ob02515d Taejun Eom 1 , Anzar Khan
Affiliation
The aim of this work is to show that by increasing the number of donor substituents in a donor/acceptor system, the sensitivity of the azobenzene linkage towards a reductive cleavage reaction can be enhanced to unprecedented high levels. For instance, in a triple-donor system, less than a second constitutes the half-life of the azo (N[double bond, length as m-dash]N) bond. Synthetic access to such redox active scaffolds is highly practical and requires only 1-2 synthetic steps. The fundamental molecular design is also adaptable. This is demonstrated through scaffold functionalization by azide, tetraethylene glycol, and biotin groups. The availability of the azide group is shown in a copper-free 'click' reaction suitable in context with protein conjugation and proteomics application. Finally, the clean nature of the scission process is demonstrated with the help of liquid chromatography coupled with mass analysis. This work, therefore, describes development of cleavable azobenzene linkers that can be accessed with synthetic ease, can be multiply functionalized, and show a clean and rapid response to mild reducing conditions.
中文翻译:
过敏性偶氮苯:易于合成具有可调和高还原性的可点击和可裂解的偶氮接头。
这项工作的目的是表明,通过增加供体/受体体系中供体取代基的数量,可以将偶氮苯键对还原裂解反应的敏感性提高到前所未有的高水平。例如,在三供体系统中,小于一秒构成偶氮(N [双键,长度为m-N]的长度)键的半衰期。合成获得这种氧化还原活性支架的方法非常实用,仅需1-2个合成步骤。基本的分子设计也是可适应的。这通过叠氮化物,四甘醇和生物素基团对支架的官能化来证明。叠氮化物基团的可用性在无铜“点击”反应中显示出来,适用于蛋白质结合和蛋白质组学应用。最后,液相色谱与质量分析相结合,证明了分裂过程的清洁性质。因此,这项工作描述了可裂解的偶氮苯连接基的开发,该连接基可以合成简便地获得,可以被多重官能化,并且显示出对轻度还原条件的清洁而快速的响应。
更新日期:2020-01-06
中文翻译:
过敏性偶氮苯:易于合成具有可调和高还原性的可点击和可裂解的偶氮接头。
这项工作的目的是表明,通过增加供体/受体体系中供体取代基的数量,可以将偶氮苯键对还原裂解反应的敏感性提高到前所未有的高水平。例如,在三供体系统中,小于一秒构成偶氮(N [双键,长度为m-N]的长度)键的半衰期。合成获得这种氧化还原活性支架的方法非常实用,仅需1-2个合成步骤。基本的分子设计也是可适应的。这通过叠氮化物,四甘醇和生物素基团对支架的官能化来证明。叠氮化物基团的可用性在无铜“点击”反应中显示出来,适用于蛋白质结合和蛋白质组学应用。最后,液相色谱与质量分析相结合,证明了分裂过程的清洁性质。因此,这项工作描述了可裂解的偶氮苯连接基的开发,该连接基可以合成简便地获得,可以被多重官能化,并且显示出对轻度还原条件的清洁而快速的响应。