Methods for converting cysteine to dehydroalanine on peptides and proteins
Justin M. Chalker(University of Oxford), Smita B. Gunnoo(University of Oxford), Omar Boutureira(University of Oxford), Stefanie Gerstberger(University of Oxford), Marta Fernández‐González(University of Oxford), Gonçalo J. L. Bernardes(University of Oxford), Laura Griffin(UCB Pharma (United Kingdom)), Hanna Hailu(UCB Pharma (United Kingdom)), Christopher J. Schofield(University of Oxford), Benjamin G. Davis(University of Oxford)
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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.
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