Synthesis of a phosphorothioate analogue of flavin mononucleotide: reconstitution of the FMN-free form of NADPH-cytochrome P-450 reductase

Biochemistry. 1987 Aug 25;26(17):5344-50. doi: 10.1021/bi00391a019.

Abstract

The chemical synthesis of riboflavin 5'-phosphorothioate (5'-FMNS) is described. 5'-FMNS is obtained from the alkaline hydrolysis of riboflavin 4',5'-cyclic phosphorothioate, which is produced upon reaction of riboflavin (RB) with thiophosphoryl chloride in trimethyl phosphate. 5'-FMNS has been tested for enzymatic reconstitution of NADPH-cytochrome P-450 reductase (EC 1.6.2.4) depleted of its FMN prosthetic group, but containing its full complement (1 equiv) of FAD. The synthesis, purification, and characterization of 5'-FMNS are reported, and documentation of its efficacy in reconstituting the reductase by fluorometric and absorbance spectrophotometric measurements, as well as enzymatic activity, is presented. Data indicate that 5'-FMNS is totally competent in reconstituting NADPH-cytochrome c reductase activity, which requires the presence of both FAD and a flavin mononucleotide, and its fluorescence is completely quenched upon addition to FMN-free NADPH-cytochrome P-450 reductase.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Flavin Mononucleotide / isolation & purification
  • Flavin Mononucleotide / metabolism
  • Indicators and Reagents
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • NADPH-Ferrihemoprotein Reductase / metabolism*
  • Protein Binding
  • Riboflavin / analogs & derivatives*
  • Riboflavin / chemical synthesis
  • Riboflavin / metabolism
  • Spectrometry, Fluorescence
  • Spectrophotometry

Substances

  • Indicators and Reagents
  • riboflavin 5'-phosphorothioate
  • Flavin Mononucleotide
  • NADPH-Ferrihemoprotein Reductase
  • Riboflavin