Issue 84, 2018

Reviving old protecting group chemistry for site-selective peptide–protein conjugation

Abstract

Methodologies to conjugate proteins to property-enhancing entities are highly sought after. We report a remarkably simple strategy for conjugating proteins bearing accessible cysteines to unprotected peptides containing a Cys(Scm) protecting group, which is introduced on-resin via a Cys(Acm) building block. The peptides employed for this proof of principle study are highly varied and structurally diverse, and undergo multiple on-resin decoration steps prior to conjugation. The methodology was applied to three different proteins, and proved to be efficient and site-selective. This twist on protecting group chemistry has led to a novel and generally applicable strategy for crossed-disulfide formation between proteins and peptides.

Graphical abstract: Reviving old protecting group chemistry for site-selective peptide–protein conjugation

Supplementary files

Article information

Article type
Communication
Submitted
16 Aug 2018
Accepted
28 Sep 2018
First published
01 Okt 2018

Chem. Commun., 2018,54, 11929-11932

Reviving old protecting group chemistry for site-selective peptide–protein conjugation

S. B. Gunnoo, A. Iyer, W. Vannecke, K. W. Decoene, T. Hebbrecht, J. Gettemans, M. Laga, S. Loverix, I. Lasters and A. Madder, Chem. Commun., 2018, 54, 11929 DOI: 10.1039/C8CC06684A

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