Olefin Cross-Metathesis on Proteins: Investigation of Allylic Chalcogen Effects and Guiding Principles in Metathesis Partner Selection

Yuya Lin, Justin Chalker, Benjamin Davis

    Research output: Contribution to journalArticlepeer-review

    132 Citations (Scopus)

    Abstract

    Olefin metathesis has recently emerged as a viable reaction for chemical protein modification. The scope and limitations of olefin metathesis in bioconjugation, however, remain unclear. Herein we report an assessment of various factors that contribute to productive cross-metathesis on protein substrates. Sterics, substrate scope, and linker selection are all considered. It was discovered during this investigation that allyl chalcogenides generally enhance the rate of alkene metathesis reactions. Allyl selenides were found to be exceptionally reactive olefin metathesis substrates, enabling a broad range of protein modifications not previously possible. The principles considered in this report are important not only for expanding the repertoire of bioconjugation but also for the application of olefin metathesis in general synthetic endeavors.

    Original languageEnglish
    Pages (from-to)16805-16811
    Number of pages7
    JournalJournal of The American Chemical Society
    Volume132
    Issue number47
    DOIs
    Publication statusPublished - 1 Dec 2010

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