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Allyl sulfides are privileged substrates in aqueous cross-metathesis: application to site-selective protein modification.

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.
Publication status:
Published

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Publisher copy:
10.1021/ja8026168

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
Journal of the American Chemical Society
Volume:
130
Issue:
30
Pages:
9642-9643
Publication date:
2008-07-05
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
URN:
uuid:1b6eb320-c78c-400d-b5df-235389590684
Source identifiers:
34292
Local pid:
pubs:34292

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