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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 publication

DOI

10.1021/ja104994d

Type

Journal article

Journal

J Am Chem Soc

Publication Date

01/12/2010

Volume

132

Pages

16805 - 16811

Keywords

Alkenes, Bacillus, Chalcogens, Cysteine, Models, Molecular, Protein Conformation, Proteins, Subtilisin, Water