Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Tilden, James A. R., Lubben, Anneke T., Reeksting, Shaun B., Kociok‐Köhn, Gabriele, Frost, Christopher G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
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
_version_ 1784752291180445696
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
work_keys_str_mv AT tildenjamesar pdiimediatedchactivationforcysteinebioconjugation
AT lubbenanneket pdiimediatedchactivationforcysteinebioconjugation
AT reekstingshaunb pdiimediatedchactivationforcysteinebioconjugation
AT kociokkohngabriele pdiimediatedchactivationforcysteinebioconjugation
AT frostchristopherg pdiimediatedchactivationforcysteinebioconjugation