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Issue 84, 2018
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Reviving old protecting group chemistry for site-selective peptide–protein conjugation

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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

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Publication details

The article was received on 16 Aug 2018, accepted on 28 Sep 2018 and first published on 01 Oct 2018


Article type: Communication
DOI: 10.1039/C8CC06684A
Citation: Chem. Commun., 2018,54, 11929-11932

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    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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