Methods for converting cysteine to dehydroalanine on peptides and proteins

Justin Chalker; Smita Gunnoo; Omar Boutureira; Stefanie Gerstberger; Marta Fernandez-Gonzalez; Goncalo Bernardes; Laura Griffin; Hanna Hailu; Christopher Schofield; Benjamin Davis

doi:10.1039/c1sc00185j

Methods for converting cysteine to dehydroalanine on peptides and proteins

Justin Chalker, Smita Gunnoo, Omar Boutureira, Stefanie Gerstberger, Marta Fernandez-Gonzalez, Goncalo Bernardes, Laura Griffin, Hanna Hailu, Christopher Schofield, Benjamin Davis

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255 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1666-1676
Number of pages	11
Journal	Chemical Science
Volume	2
Issue number	9
DOIs	https://doi.org/10.1039/c1sc00185j
Publication status	Published - Sept 2011

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AU - Chalker, Justin

AU - Gunnoo, Smita

AU - Boutureira, Omar

AU - Gerstberger, Stefanie

AU - Fernandez-Gonzalez, Marta

AU - Bernardes, Goncalo

AU - Griffin, Laura

AU - Hailu, Hanna

AU - Schofield, Christopher

AU - Davis, Benjamin

PY - 2011/9

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N2 - 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.

AB - 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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Methods for converting cysteine to dehydroalanine on peptides and proteins

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