Palladium−Peptide Oxidative Addition Complexes for Bioconjugation

Abstract

The synthesis of palladium oxidative addition complexes derived from unprotected peptides is described. Incorporation of 4-halophenylalanine into a peptide during solid phase peptide synthesis allows for subsequent oxidative addition at this position upon treatment with a palladium precursor and suitable ligand. The resulting palladium−peptide complexes are solid, storable, water-soluble, and easily purified via high-performance liquid chromatography. These complexes react with thiols in aqueous buffer, offering an efficient method for bioconjugation. Using this strategy, peptides can be functionalized with small molecules to prepare modified aryl thioether side-chains at low micromolar concentrations. Additionally, peptide−peptide and peptide−protein ligations are demonstrated under dilute aqueous conditions.

Supplementary files

Article information

Article type
Edge Article
Submitted
21 Jul 2022
Accepted
19 Sep 2022
First published
19 Sep 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022, Accepted Manuscript

Palladium−Peptide Oxidative Addition Complexes for Bioconjugation

A. J. Rojas, J. M. Wolfe, H. H. Dhanjee, I. Buslov, N. L. Truex, R. Y. Liu, W. Massefski, B. Pentelute and S. L. Buchwald, Chem. Sci., 2022, Accepted Manuscript , DOI: 10.1039/D2SC04074C

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements