Cyclotrimerization of phenylacetylene catalyzed by a cobalt half-sandwich complex embedded in an engineered variant of transmembrane protein FhuA

Org Biomol Chem. 2018 Aug 1;16(30):5452-5456. doi: 10.1039/c8ob01369a.

Abstract

An (η5-cyclopentadienyl)cobalt(i) complex was covalently incorporated into an engineered variant of the transmembrane protein ferric hydroxamate uptake protein component: A, FhuA ΔCVFtev, using a thiol-ene reaction. A CD spectrum shows the structural integrity of the biohybrid catalyst. MALDI-TOF of the segment containing the anchoring site for the cobalt complex Cys545 confirmed successful conjugation. This biohybrid catalyst catalyzed the cyclotrimerization of phenylacetylene to give a mixture of regioisomeric 1,2,4- and 1,3,5-triphenylbenzene in aqueous medium.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylene / analogs & derivatives*
  • Acetylene / chemistry
  • Acetylene / metabolism
  • Bacterial Outer Membrane Proteins / chemistry*
  • Bacterial Outer Membrane Proteins / genetics
  • Bacterial Outer Membrane Proteins / metabolism
  • Catalysis
  • Cobalt / chemistry*
  • Coordination Complexes / chemistry*
  • Cyclization
  • Dimerization
  • Escherichia coli / chemistry*
  • Escherichia coli / genetics
  • Escherichia coli / metabolism
  • Escherichia coli Proteins / chemistry*
  • Escherichia coli Proteins / genetics
  • Escherichia coli Proteins / metabolism
  • Ferric Compounds / metabolism
  • Hydroxamic Acids / metabolism
  • Models, Molecular
  • Protein Engineering

Substances

  • Bacterial Outer Membrane Proteins
  • Coordination Complexes
  • Escherichia coli Proteins
  • Ferric Compounds
  • FhuA protein, E coli
  • Hydroxamic Acids
  • iron (III) hydroxamate
  • phenylacetylene
  • Cobalt
  • Acetylene