Cargando…

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

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Eising, Selma, Lelivelt, Francis, Bonger, Kimberly M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5113785/
https://www.ncbi.nlm.nih.gov/pubmed/27605057
http://dx.doi.org/10.1002/anie.201605271
_version_ 1782468244761739264
author Eising, Selma
Lelivelt, Francis
Bonger, Kimberly M.
author_facet Eising, Selma
Lelivelt, Francis
Bonger, Kimberly M.
author_sort Eising, Selma
collection PubMed
description 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‐s‐tetrazines is described. Depending on the substituents, VBA derivatives give second‐order rate constants up to 27 m (−1) s(−1) 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.
format Online
Article
Text
id pubmed-5113785
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-51137852016-12-02 Vinylboronic Acids as Fast Reacting, Synthetically Accessible, and Stable Bioorthogonal Reactants in the Carboni–Lindsey Reaction Eising, Selma Lelivelt, Francis Bonger, Kimberly M. Angew Chem Int Ed Engl Communications 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‐s‐tetrazines is described. Depending on the substituents, VBA derivatives give second‐order rate constants up to 27 m (−1) s(−1) 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. John Wiley and Sons Inc. 2016-09-08 2016-09-26 /pmc/articles/PMC5113785/ /pubmed/27605057 http://dx.doi.org/10.1002/anie.201605271 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Eising, Selma
Lelivelt, Francis
Bonger, Kimberly M.
Vinylboronic Acids as Fast Reacting, Synthetically Accessible, and Stable Bioorthogonal Reactants in the Carboni–Lindsey Reaction
title Vinylboronic Acids as Fast Reacting, Synthetically Accessible, and Stable Bioorthogonal Reactants in the Carboni–Lindsey Reaction
title_full Vinylboronic Acids as Fast Reacting, Synthetically Accessible, and Stable Bioorthogonal Reactants in the Carboni–Lindsey Reaction
title_fullStr Vinylboronic Acids as Fast Reacting, Synthetically Accessible, and Stable Bioorthogonal Reactants in the Carboni–Lindsey Reaction
title_full_unstemmed Vinylboronic Acids as Fast Reacting, Synthetically Accessible, and Stable Bioorthogonal Reactants in the Carboni–Lindsey Reaction
title_short Vinylboronic Acids as Fast Reacting, Synthetically Accessible, and Stable Bioorthogonal Reactants in the Carboni–Lindsey Reaction
title_sort vinylboronic acids as fast reacting, synthetically accessible, and stable bioorthogonal reactants in the carboni–lindsey reaction
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5113785/
https://www.ncbi.nlm.nih.gov/pubmed/27605057
http://dx.doi.org/10.1002/anie.201605271
work_keys_str_mv AT eisingselma vinylboronicacidsasfastreactingsyntheticallyaccessibleandstablebioorthogonalreactantsinthecarbonilindseyreaction
AT leliveltfrancis vinylboronicacidsasfastreactingsyntheticallyaccessibleandstablebioorthogonalreactantsinthecarbonilindseyreaction
AT bongerkimberlym vinylboronicacidsasfastreactingsyntheticallyaccessibleandstablebioorthogonalreactantsinthecarbonilindseyreaction