Boronic acids facilitate rapid oxime condensations at neutral pH
Boronic acids facilitate rapid oxime condensations at neutral pH
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DOI：
10.1039/c5sc00921a
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发表时间：
2015-01-01
期刊：
影响因子：
8.4
通讯作者：
Gillingham, Dennis
中科院分区：
文献类型：
--
作者：
Schmidt, Pascal;Stress, Cedric;Gillingham, Dennis
We report here the discovery and development of boron-assisted oxime formation as a powerful connective reaction for chemical biology. Oximes proximal to boronic acids form in neutral aqueous buffer with rate constants of more than 10(4) M-1 s(-1), the largest to date for any oxime condensation. Boron's dynamic coordination chemistry confers an adaptability that seems to aid a number of elementary steps in the oxime condensation. In addition to applications in bioconjugation, the emerging importance of boronic acids in chemical biology as carbohydrate receptors or peroxide probes, and the growing list of drugs and drug candidates containing boronic acids suggest many potential applications.
