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 journalArticle

    166 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 languageEnglish
    Pages (from-to)1666-1676
    Number of pages11
    JournalChemical Science
    Volume2
    Issue number9
    DOIs
    Publication statusPublished - 2011

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

  • Cite this

    Chalker, J., Gunnoo, S., Boutureira, O., Gerstberger, S., Fernandez-Gonzalez, M., Bernardes, G., Griffin, L., Hailu, H., Schofield, C., & Davis, B. (2011). Methods for converting cysteine to dehydroalanine on peptides and proteins. Chemical Science, 2(9), 1666-1676. https://doi.org/10.1039/c1sc00185j