Enhanced photochemical [6π] electrocyclization within the lipophilic protein binding site

Org Lett. 2012 Apr 6;14(7):1788-91. doi: 10.1021/ol3003805. Epub 2012 Mar 14.

Abstract

Photocyclization of N-methyldiphenylamine to N-methylcarbazole is achieved within the microenvironment provided by site I of serum albumins. Quantum yield determinations, combined with transient absorption spectroscopic detection of the dihydrocarbazole intermediate, demonstrate that protein encapsulation provides a subtle control of the kinetic parameters, leading to optimized efficiencies.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemistry
  • Animals
  • Binding Sites
  • Carbazoles / chemistry
  • Cattle
  • Cyclization
  • Humans
  • Kinetics
  • Models, Chemical
  • Molecular Structure
  • Protein Binding
  • Serum Albumin / chemistry*

Substances

  • Aniline Compounds
  • Carbazoles
  • Serum Albumin
  • N-methylcarbazole