Allyl Sulfides Are Privileged Substrates in Aqueous Cross-Metathesis: Application to Site-Selective Protein Modification

Yuya A. Lin, Justin M. Chalker, Nicola Floyd, Gonalo J. L. Bernardes and Benjamin G. Davis
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, U.K.
J. Am. Chem. Soc., 2008, 130 (30), pp 9642–9643
DOI: 10.1021/ja8026168
Publication Date (Web): July 1, 2008
Copyright © 2008 American Chemical Society

Abstract

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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.

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History

  • Published In Issue July 30, 2008
  • Article ASAPJuly 01, 2008
  • Received: April 09, 2008

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