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Optimized Aqueous Kinugasa Reactions for Bioorthogonal Chemistry Applications

Abstract

Kinugasa reactions hold potential for bioorthogonal chemistry in that the reagents can be biocompatible. Unlike other bioorthogonal reaction products, β-lactams are potentially reactive, which can be useful for synthesizing new biomaterials. A limiting factor for applications consists of slow reaction rates. Herein we report an optimized aqueous copper(I)-catalyzed alkyne-nitrone cycloaddition involving rearrangement (CuANCR) with rate accelerations made possible by the use of surfactant micelles. We have investigated the factors that accelerate the aqueous CuANCR reaction and demonstrate enhanced modification of a model membrane-associated peptide. We discovered that lipids/surfactants and alkyne structure have a significant impact on the reaction rate, with biological lipids and electron-poor alkynes showing greater reactivity. These new findings have implications for the use of CuANCR for modifying integral membrane proteins as well as live cell labelling and other bioorthogonal applications.

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Supplementary files

Article information


Submitted
05 Dec 2019
Accepted
08 Jan 2020
First published
10 Jan 2020

Chem. Commun., 2020, Accepted Manuscript
Article type
Communication

Optimized Aqueous Kinugasa Reactions for Bioorthogonal Chemistry Applications

D. A. Bilodeau, K. Margison, N. Ahmed, M. Strmiskova, A. Sherratt and J. P. Pezacki, Chem. Commun., 2020, Accepted Manuscript , DOI: 10.1039/C9CC09473C

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