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Pd(II)‐Mediated C−H Activation for Cysteine Bioconjugation
Selective bioconjugation remains a significant challenge for the synthetic chemist due to the stringent reaction conditions required by biomolecules coupled with their high degree of functionality. The current trailblazer of transition‐metal mediated bioconjugation chemistry involves the use of Pd(I...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9305290/ https://www.ncbi.nlm.nih.gov/pubmed/34905636 http://dx.doi.org/10.1002/chem.202104385 |
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author | Tilden, James A. R. Lubben, Anneke T. Reeksting, Shaun B. Kociok‐Köhn, Gabriele Frost, Christopher G. |
author_facet | Tilden, James A. R. Lubben, Anneke T. Reeksting, Shaun B. Kociok‐Köhn, Gabriele Frost, Christopher G. |
author_sort | Tilden, James A. R. |
collection | PubMed |
description | Selective bioconjugation remains a significant challenge for the synthetic chemist due to the stringent reaction conditions required by biomolecules coupled with their high degree of functionality. The current trailblazer of transition‐metal mediated bioconjugation chemistry involves the use of Pd(II) complexes prepared via an oxidative addition process. Herein, the preparation of Pd(II) complexes for cysteine bioconjugation via a facile C−H activation process is reported. These complexes show bioconjugation efficiency competitive with what is seen in the current literature, with a user‐friendly synthesis, common Pd(II) sources, and a more cost‐effective ligand. Furthermore, these complexes need not be isolated, and still achieve high conversion efficiency and selectivity of a model peptide. These complexes also demonstrate the ability to selectively arylate a single surface cysteine residue on a model protein substrate, further demonstrating their utility. |
format | Online Article Text |
id | pubmed-9305290 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-93052902022-07-28 Pd(II)‐Mediated C−H Activation for Cysteine Bioconjugation Tilden, James A. R. Lubben, Anneke T. Reeksting, Shaun B. Kociok‐Köhn, Gabriele Frost, Christopher G. Chemistry Research Articles Selective bioconjugation remains a significant challenge for the synthetic chemist due to the stringent reaction conditions required by biomolecules coupled with their high degree of functionality. The current trailblazer of transition‐metal mediated bioconjugation chemistry involves the use of Pd(II) complexes prepared via an oxidative addition process. Herein, the preparation of Pd(II) complexes for cysteine bioconjugation via a facile C−H activation process is reported. These complexes show bioconjugation efficiency competitive with what is seen in the current literature, with a user‐friendly synthesis, common Pd(II) sources, and a more cost‐effective ligand. Furthermore, these complexes need not be isolated, and still achieve high conversion efficiency and selectivity of a model peptide. These complexes also demonstrate the ability to selectively arylate a single surface cysteine residue on a model protein substrate, further demonstrating their utility. John Wiley and Sons Inc. 2022-01-12 2022-02-21 /pmc/articles/PMC9305290/ /pubmed/34905636 http://dx.doi.org/10.1002/chem.202104385 Text en © 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Research Articles Tilden, James A. R. Lubben, Anneke T. Reeksting, Shaun B. Kociok‐Köhn, Gabriele Frost, Christopher G. Pd(II)‐Mediated C−H Activation for Cysteine Bioconjugation |
title | Pd(II)‐Mediated C−H Activation for Cysteine Bioconjugation |
title_full | Pd(II)‐Mediated C−H Activation for Cysteine Bioconjugation |
title_fullStr | Pd(II)‐Mediated C−H Activation for Cysteine Bioconjugation |
title_full_unstemmed | Pd(II)‐Mediated C−H Activation for Cysteine Bioconjugation |
title_short | Pd(II)‐Mediated C−H Activation for Cysteine Bioconjugation |
title_sort | pd(ii)‐mediated c−h activation for cysteine bioconjugation |
topic | Research Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9305290/ https://www.ncbi.nlm.nih.gov/pubmed/34905636 http://dx.doi.org/10.1002/chem.202104385 |
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