Methods for converting cysteine to dehydroalanine on peptides and proteins (original) (raw)
* Corresponding authors
a Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford, United Kingdom
E-mail: ben.davis@chem.ox.ac.uk
Fax: +44 (0) 1865 285002
Tel: +44 (0) 1865 275652
b UCB Celltech, 208 Bath Road, Slough, Berkshire, United Kingdom
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.
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Article information
DOI
https://doi.org/10.1039/C1SC00185J
Article type
Edge Article
Submitted
24 Mar 2011
Accepted
18 May 2011
First published
07 Jun 2011
Download 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, 1666DOI: 10.1039/C1SC00185J
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