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Issue 23, 2021
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Plasma induced acceleration and selectivity in strain-promoted azide–alkyne cycloadditions

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Abstract

Strain-promoted azide–alkyne cycloaddition (SPAAC) is an important member of the bioorthogonal reaction family. Over the past decade, much work has been dedicated to the generation of new strained alkynes with improved reactivity. While kinetics studies of SPAAC are often conducted in organic solvents, buffered solutions or mixtures, these media do not reflect the complexity of in vivo systems. In this work, we show that performing SPAAC in human plasma leads to intriguing kinetics and selectivity effects. In particular, we observed that reactions in plasma could be accelerated up to 70-fold compared to those in methanol, and that selective couplings between a pair of reagents could be possible in competition experiments. These findings highlight the value of evaluating bioorthogonal reactions in such a complex medium, especially when in vivo applications are planned, as unsuspected behaviour can be observed, disrupting the usual rules governing the reactivity in simple solvent systems.

Graphical abstract: Plasma induced acceleration and selectivity in strain-promoted azide–alkyne cycloadditions

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Supplementary files

Article information


Submitted
18 Mar 2021
Accepted
04 May 2021
First published
05 May 2021

Org. Biomol. Chem., 2021,19, 5063-5067
Article type
Communication

Plasma induced acceleration and selectivity in strain-promoted azide–alkyne cycloadditions

D. Warther, E. Dursun, M. Recher, S. Ursuegui, M. Mosser, J. Sobska, W. Krezel, G. Chaubet and A. Wagner, Org. Biomol. Chem., 2021, 19, 5063
DOI: 10.1039/D1OB00529D

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