Vinylboronic Acids as Fast Reacting, Synthetically Accessible, and Stable Bioorthogonal Reactants in the Carboni–Lindsey Reaction

Selma Eising, Francis Lelivelt, Kimberly M. Bonger

doi:10.1002/anie.201605271

Vinylboronic Acids as Fast Reacting, Synthetically Accessible, and Stable Bioorthogonal Reactants in the Carboni–Lindsey Reaction

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Selma Eising

Department of Biomolecular Chemistry Institute for Molecules and Materials Radboud University Heyendaalseweg 135 6525 AJ Nijmegen The Netherlands
Francis Lelivelt

Department of Biomolecular Chemistry Institute for Molecules and Materials Radboud University Heyendaalseweg 135 6525 AJ Nijmegen The Netherlands
Kimberly M. Bonger

Department of Biomolecular Chemistry Institute for Molecules and Materials Radboud University Heyendaalseweg 135 6525 AJ Nijmegen The Netherlands

書誌事項

公開日: 2016-09-08

権利情報

http://creativecommons.org/licenses/by-nc-nd/4.0/

DOI

10.1002/anie.201605271

公開者: Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>Bioorthogonal reactions are widely used for the chemical modification of biomolecules. The application of vinylboronic acids (VBAs) as non‐strained, synthetically accessible and water‐soluble reaction partners in a bioorthogonal inverse electron‐demand Diels–Alder (iEDDA) reaction with 3,6‐dipyridyl‐<jats:italic>s</jats:italic>‐tetrazines is described. Depending on the substituents, VBA derivatives give second‐order rate constants up to 27 <jats:sc>m</jats:sc><jats:sup>−1</jats:sup> s<jats:sup>−1</jats:sup> in aqueous environments at room temperature, which is suitable for biological labeling applications. The VBAs are shown to be biocompatible, non‐toxic, and highly stable in aqueous media and cell lysate. Furthermore, VBAs can be used orthogonally to the strain‐promoted alkyne–azide cycloaddition for protein modification, making them attractive complements to the bioorthogonal molecular toolbox.</jats:p>