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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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Supplementary files

Article information


Submitted
24 Mar 2011
Accepted
18 May 2011
First published
07 Jun 2011

Chem. Sci., 2011,2, 1666-1676
Article type
Edge Article

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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