Abstract
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.
MeSH terms
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Allyl Compounds / chemistry*
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Bacillus / enzymology
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Bacterial Proteins / chemistry*
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Cysteine / analogs & derivatives
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Cysteine / chemistry
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Escherichia coli / genetics
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Escherichia coli / metabolism
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Glucosidases / chemistry
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Glucosidases / genetics
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Glucosidases / metabolism
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Methionine / chemistry
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Methionine / genetics
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Methionine / metabolism
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Models, Molecular
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Subtilisin / chemistry
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Sulfides / chemistry*
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Water / chemistry
Substances
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Allyl Compounds
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Bacterial Proteins
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Sulfides
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Water
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allyl sulfide
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S-allylcysteine
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Methionine
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Glucosidases
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Sulfolobus solfataricus beta-glycosidase
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Subtilisin
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Cysteine