Boronic acids facilitate rapid oxime condensations at neutral pH

Schmidt, Pascal and Stress, Cedric and Gillingham, Dennis. (2015) Boronic acids facilitate rapid oxime condensations at neutral pH. Chemical Science, 6. pp. 3329-3333.

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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 104 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.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Organische Chemie (Gillingham)
UniBasel Contributors:Gillingham, Dennis and Schmidt, Pascal
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Royal Society of Chemistry
Note:Publication type according to Uni Basel Research Database: Journal article
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edoc DOI:
Last Modified:17 Mar 2017 13:05
Deposited On:21 Apr 2016 15:21

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