N-Terminal Cysteine Bioconjugation with (2-Cyanamidophenyl)boronic Acids Enables the Direct Formation of Benzodiazaborines on Peptides

[Image: see text] Benzodiazaborines (BDABs) have emerged as a valuable tool to produce stable and functional bioconjugates via a click-type transformation. However, the current available methods to install them on peptides lack bioorthogonality, limiting their applications. Here, we report a strateg...

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Autores principales: Padanha, Rita, Cavadas, Rafaela A. N., Merino, Pedro, António, João P. M., Gois, Pedro M. P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10391619/
https://www.ncbi.nlm.nih.gov/pubmed/37466099
http://dx.doi.org/10.1021/acs.orglett.3c01835
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author Padanha, Rita
Cavadas, Rafaela A. N.
Merino, Pedro
António, João P. M.
Gois, Pedro M. P.
author_facet Padanha, Rita
Cavadas, Rafaela A. N.
Merino, Pedro
António, João P. M.
Gois, Pedro M. P.
author_sort Padanha, Rita
collection PubMed
description [Image: see text] Benzodiazaborines (BDABs) have emerged as a valuable tool to produce stable and functional bioconjugates via a click-type transformation. However, the current available methods to install them on peptides lack bioorthogonality, limiting their applications. Here, we report a strategy to install BDABs directly on peptide chains using (2-cyanamidophenyl)boronic acids (2CyPBAs). The resulting BDAB is stabilized through the formation of a key intramolecular B–N bond. This technology was applied in the selective modification of N-terminal cysteine-containing functional peptides.
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spelling pubmed-103916192023-08-02 N-Terminal Cysteine Bioconjugation with (2-Cyanamidophenyl)boronic Acids Enables the Direct Formation of Benzodiazaborines on Peptides Padanha, Rita Cavadas, Rafaela A. N. Merino, Pedro António, João P. M. Gois, Pedro M. P. Org Lett [Image: see text] Benzodiazaborines (BDABs) have emerged as a valuable tool to produce stable and functional bioconjugates via a click-type transformation. However, the current available methods to install them on peptides lack bioorthogonality, limiting their applications. Here, we report a strategy to install BDABs directly on peptide chains using (2-cyanamidophenyl)boronic acids (2CyPBAs). The resulting BDAB is stabilized through the formation of a key intramolecular B–N bond. This technology was applied in the selective modification of N-terminal cysteine-containing functional peptides. American Chemical Society 2023-07-19 /pmc/articles/PMC10391619/ /pubmed/37466099 http://dx.doi.org/10.1021/acs.orglett.3c01835 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Padanha, Rita
Cavadas, Rafaela A. N.
Merino, Pedro
António, João P. M.
Gois, Pedro M. P.
N-Terminal Cysteine Bioconjugation with (2-Cyanamidophenyl)boronic Acids Enables the Direct Formation of Benzodiazaborines on Peptides
title N-Terminal Cysteine Bioconjugation with (2-Cyanamidophenyl)boronic Acids Enables the Direct Formation of Benzodiazaborines on Peptides
title_full N-Terminal Cysteine Bioconjugation with (2-Cyanamidophenyl)boronic Acids Enables the Direct Formation of Benzodiazaborines on Peptides
title_fullStr N-Terminal Cysteine Bioconjugation with (2-Cyanamidophenyl)boronic Acids Enables the Direct Formation of Benzodiazaborines on Peptides
title_full_unstemmed N-Terminal Cysteine Bioconjugation with (2-Cyanamidophenyl)boronic Acids Enables the Direct Formation of Benzodiazaborines on Peptides
title_short N-Terminal Cysteine Bioconjugation with (2-Cyanamidophenyl)boronic Acids Enables the Direct Formation of Benzodiazaborines on Peptides
title_sort n-terminal cysteine bioconjugation with (2-cyanamidophenyl)boronic acids enables the direct formation of benzodiazaborines on peptides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10391619/
https://www.ncbi.nlm.nih.gov/pubmed/37466099
http://dx.doi.org/10.1021/acs.orglett.3c01835
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