Olefin metathesis for chemical biology

Curr Opin Chem Biol. 2008 Dec;12(6):767-73. doi: 10.1016/j.cbpa.2008.09.022. Epub 2008 Oct 18.

Abstract

Chemical biology relies on effective synthetic chemistry for building molecules to probe and modulate biological function. Olefin metathesis in organic solvents is a valuable addition to this armamentarium, and developments during the previous decade are enabling metathesis in aqueous solvents for the manipulation of biomolecules. Functional group-tolerant ruthenium metathesis catalysts modified with charged moieties or hydrophilic polymers are soluble and active in water, enabling ring-opening metathesis polymerization, cross metathesis, and ring-closing metathesis. Alternatively, conventional hydrophobic ruthenium complexes catalyze a similar array of metathesis reactions in mixtures of water and organic solvents. This strategy has enabled cross metathesis on the surface of a protein. Continuing developments in catalyst design and methodology will popularize the bioorthogonal reactivity of metathesis.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Review

MeSH terms

  • Alkenes / chemistry*
  • Heterocyclic Compounds / chemistry
  • Phosphines / chemistry
  • Polymers / chemistry
  • Proteins / chemistry
  • Solubility

Substances

  • Alkenes
  • Heterocyclic Compounds
  • Phosphines
  • Polymers
  • Proteins
  • phosphine