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Issue 9, 2011
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Methods for converting cysteine to dehydroalanine on peptides and proteins

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Abstract

Dehydroalanine is a synthetic precursor to a wide array of protein modifications. We describe multiple methods for the chemical conversion of cysteine to dehydroalanine on peptides and proteins. The scope and limitations of these methods were investigated with attention paid to side reactions, scale, and aqueous- and bio-compatibility. The most general method investigated—a bis-alkylation–elimination of cysteine to dehydroalanine—was applied successfully to multiple proteins and enabled the site-selective synthesis of a glycosylated antibody.

Graphical abstract: Methods for converting cysteine to dehydroalanine on peptides and proteins

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Publication details

The article was received on 24 Mar 2011, accepted on 18 May 2011 and first published on 07 Jun 2011


Article type: Edge Article
DOI: 10.1039/C1SC00185J
Citation: Chem. Sci., 2011,2, 1666-1676
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    Methods for converting cysteine to dehydroalanine on peptides and proteins

    J. M. Chalker, S. B. Gunnoo, O. Boutureira, S. C. Gerstberger, M. Fernández-González, G. J. L. Bernardes, L. Griffin, H. Hailu, C. J. Schofield and B. G. Davis, Chem. Sci., 2011, 2, 1666
    DOI: 10.1039/C1SC00185J

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