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Allyl sulfides undergo efficient cross-metathesis in aqueous media with Hoveyda-Grubbs second generation catalyst 1. The high reactivity of allyl sulfides in cross-metathesis was exploited in the first examples of cross-metathesis on a protein surface. S-Allylcysteine was incorporated chemically into the protein, providing the requisite allyl sulfide handle. Preliminary efforts to genetically incorporate S-allylcysteine into proteins are also reported.

Original publication

DOI

10.1021/ja8026168

Type

Journal article

Journal

J Am Chem Soc

Publication Date

30/07/2008

Volume

130

Pages

9642 - 9643

Keywords

Allyl Compounds, Bacillus, Bacterial Proteins, Cysteine, Escherichia coli, Glucosidases, Methionine, Models, Molecular, Subtilisin, Sulfides, Water