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Olefin Metathesis for Site‐Selective Protein Modification
Author(s) -
Lin Yuya A.,
Chalker Justin M.,
Davis Benjamin G.
Publication year - 2009
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200900002
Subject(s) - olefin metathesis , metathesis , salt metathesis reaction , chemistry , combinatorial chemistry , olefin fiber , acyclic diene metathesis , aqueous medium , aqueous solution , organic chemistry , catalysis , polymerization , polymer
Protein compatible . Olefin metathesis has emerged as a viable strategy for site‐selective protein modification. This minireview traces its development from early peptide models and metathesis in water to its ultimate application to protein substrates. Prospects in chemistry and biology are also discussed.For a reaction to be generally useful for protein modification, it must be site‐selective and efficient under conditions compatible with proteins: aqueous media, low to ambient temperature, and at or near neutral pH. To engineer a reaction that satisfies these conditions is not a simple task. Olefin metathesis is one of most useful reactions for carbon–carbon bond formation, but does it fit these requirements? This minireview is an account of the development of olefin metathesis for protein modification. Highlighted below are examples of olefin metathesis in peptidic systems and in aqueous media that laid the groundwork for successful metathesis on protein substrates. Also discussed are the opportunities in protein engineering for the genetic introduction of amino acids suitable for metathesis and the related challenges in chemistry and biology.