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Issue 32, 2016
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The role of boronic acids in accelerating condensation reactions of α-effect amines with carbonyls

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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.

Graphical abstract: The role of boronic acids in accelerating condensation reactions of α-effect amines with carbonyls

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Publication details

The article was received on 01 Jun 2016, accepted on 05 Jul 2016 and first published on 18 Jul 2016


Article type: Perspective
DOI: 10.1039/C6OB01193D
Citation: Org. Biomol. Chem., 2016,14, 7606-7609
  • Open access: Creative Commons BY-NC license
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    The role of boronic acids in accelerating condensation reactions of α-effect amines with carbonyls

    D. Gillingham, Org. Biomol. Chem., 2016, 14, 7606
    DOI: 10.1039/C6OB01193D

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