Artificial metalloenzymes for enantioselective catalysis based on the noncovalent incorporation of organometallic moieties in a host protein

Chemistry. 2005 Jun 20;11(13):3798-804. doi: 10.1002/chem.200401232.

Abstract

Enzymatic and homogeneous catalysis offer complementary means to produce enantiopure products. Incorporation of achiral, biotinylated aminodiphosphine-rhodium complexes in (strept)avidin affords enantioselective hydrogenation catalysts. A combined chemogenetic procedure allows the optimization of the activity and the selectivity of such artificial metalloenzymes: the reduction of acetamidoacrylate proceeds to produce N-acetamidoalanine in either 96 % ee (R) or 80 % ee (S). In addition to providing a chiral second coordination sphere and, thus, selectivity to the catalyst, the phenomenon of protein-accelerated catalysis (e.g., increased activity) was unraveled. Such artificial metalloenzymes based on the biotin-avidin technology display features that are reminiscent of both homogeneous and of enzymatic catalysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding Sites
  • Biomimetics
  • Catalysis
  • Enzymes, Immobilized / chemical synthesis*
  • Enzymes, Immobilized / chemistry
  • Models, Molecular
  • Molecular Structure
  • Multiprotein Complexes / chemical synthesis*
  • Multiprotein Complexes / chemistry
  • Organometallic Compounds / chemistry*
  • Oxidation-Reduction
  • Protein Structure, Tertiary
  • Proteins / chemistry*
  • Rhodium / chemistry*
  • Stereoisomerism
  • Streptavidin / chemistry*

Substances

  • Enzymes, Immobilized
  • Multiprotein Complexes
  • Organometallic Compounds
  • Proteins
  • Streptavidin
  • Rhodium