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The role of boronic acids in accelerating condensation reactions of [small alpha]-effect amines with carbonyls

Gillingham, Dennis. (2016) The role of boronic acids in accelerating condensation reactions of [small alpha]-effect amines with carbonyls. Organic & Biomolecular Chemistry, 14. pp. 7606-7609.

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Abstract

A broad palette of bioconjugation reactions are available for chemical biologists, but an area that still requires investigation is high-rate constant reactions. These are indispensable in certain applications, particularly for in vivo labelling. Appropriately positioned boronic acids accelerate normally sluggish Schiff base condensations of α-effect nucleophiles by five orders of magnitude – providing a new entry to the rare set of reactions that have a rate constant above 100 M−1 s−1 under physiological conditions. I summarize here a number of recent reports, including work from my own group, and outline a mechanistic picture that explains the differing behaviour of seemingly similar substrate classes.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Organische Chemie (Gillingham)
UniBasel Contributors:Gillingham, Dennis
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Royal Society of Chemistry
ISSN:1477-0520
e-ISSN:1477-0539
Note:Publication type according to Uni Basel Research Database: Journal article
Language:English
Identification Number:
Last Modified:23 Feb 2017 15:48
Deposited On:23 Feb 2017 15:48

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