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

    Research output: Contribution to journalArticlepeer-review

    255 Citations (Scopus)


    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 languageEnglish
    Pages (from-to)1666-1676
    Number of pages11
    JournalChemical Science
    Issue number9
    Publication statusPublished - Sept 2011


    Dive into the research topics of 'Methods for converting cysteine to dehydroalanine on peptides and proteins'. Together they form a unique fingerprint.

    Cite this