Artificial metalloenzymes: (strept)avidin as host for enantioselective hydrogenation by achiral biotinylated rhodium-diphosphine complexes

J Am Chem Soc. 2004 Nov 10;126(44):14411-8. doi: 10.1021/ja0476718.

Abstract

We report on the generation of artificial metalloenzymes based on the noncovalent incorporation of biotinylated rhodium-diphosphine complexes in (strept)avidin as host proteins. A chemogenetic optimization procedure allows one to optimize the enantioselectivity for the reduction of acetamidoacrylic acid (up to 96% ee (R) in streptavidin S112G and up to 80% ee (S) in WT avidin). The association constant between a prototypical cationic biotinylated rhodium-diphosphine catalyst precursor and the host proteins was determined at neutral pH: log K(a) = 7.7 for avidin (pI = 10.4) and log K(a) = 7.1 for streptavidin (pI = 6.4). It is shown that the optimal operating conditions for the enantioselective reduction are 5 bar at 30 degrees C with a 1% catalyst loading.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylates / chemistry
  • Avidin / analogs & derivatives*
  • Avidin / biosynthesis
  • Avidin / chemistry
  • Avidin / genetics
  • Bacillus subtilis / genetics
  • Bacillus subtilis / metabolism
  • Biotin / analogs & derivatives
  • Biotin / chemistry
  • Catalysis
  • Enzymes / chemical synthesis
  • Enzymes / chemistry*
  • Hydrogenation
  • Kinetics
  • Metalloproteins / chemical synthesis
  • Metalloproteins / chemistry*
  • Models, Molecular
  • Mutagenesis, Site-Directed
  • Phosphines / chemistry*
  • Rhodium / chemistry*
  • Stereoisomerism
  • Streptavidin / analogs & derivatives*
  • Streptavidin / biosynthesis
  • Streptavidin / chemistry
  • Streptavidin / genetics

Substances

  • Acrylates
  • Enzymes
  • Metalloproteins
  • Phosphines
  • Avidin
  • Biotin
  • Streptavidin
  • Rhodium