Issue 23, 2021

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

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

Supplementary files

Article information

Article type
Communication
Submitted
18 3月 2021
Accepted
04 5月 2021
First published
05 5月 2021

Org. Biomol. Chem., 2021,19, 5063-5067

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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