Model systems for flavoenzyme activity: interplay of hydrogen bonding and aromatic stacking in cofactor redox modulation

Org Lett. 2004 Feb 5;6(3):385-8. doi: 10.1021/ol036279g.

Abstract

[structure: see text] A model system has been developed to study the synergy between aromatic stacking and hydrogen bonding in the binding of a flavin derivative. The results show that the identity of both the hydrogen bonding and pi-stacking units strongly determine the overall receptor affinity for flavin in both the oxidized and radical anion forms.

Publication types

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

MeSH terms

  • Flavin Mononucleotide / chemistry
  • Flavin Mononucleotide / metabolism*
  • Flavin-Adenine Dinucleotide / chemistry
  • Flavin-Adenine Dinucleotide / metabolism*
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oxidation-Reduction
  • Oxidoreductases / chemistry*
  • Oxidoreductases / metabolism*
  • Xanthenes / chemistry
  • Xanthenes / metabolism

Substances

  • Xanthenes
  • Flavin-Adenine Dinucleotide
  • Flavin Mononucleotide
  • Oxidoreductases