Reactivity of horseradish peroxidase compound II toward substrates: kinetic evidence for a two-step mechanism

Biochemistry. 2000 Oct 31;39(43):13201-9. doi: 10.1021/bi001150p.

Abstract

Transient kinetic analysis of biphasic, single turnover data for the reaction of 2,2'-azino-bis[3-ethylbenzthiazoline-6-sulfonic acid] (ABTS) with horseradish peroxidase (HRPC) compound II demonstrated preequilibrium binding of ABTS (k(+5) = 7.82 x 10(4) M(-)(1) s(-)(1)) prior to rate-limiting electron transfer (k(+6) = 42.1 s(-)(1)). These data were obtained using a stopped-flow method, which included ascorbate in the reaction medium to maintain a low steady-state concentration of ABTS (pseudo-first-order conditions) and to minimize absorbance changes in the Soret region due to the accumulation of ABTS cation radicals. A steady-state kinetic analysis of the reaction confirmed that the reduction of HRPC compound II by this substrate is rate-limiting in the complete peroxidase cycle. The reaction of HRPC with o-diphenols has been investigated using a chronometric method that also included ascorbate in the assay medium to minimize the effects of nonenzymic reactions involving phenol-derived radical products. This enabled the initial rates of o-diphenol oxidation at different hydrogen peroxide and o-diphenol concentrations to be determined from the lag period induced by the presence of ascorbate. The kinetic analysis resolved the reaction of HRPC compound II with o-diphenols into two steps, initial formation of an enzyme-substrate complex followed by electron transfer from the substrate to the heme. With o-diphenols that are rapidly oxidized, the heterolytic cleavage of the O-O bond of the heme-bound hydrogen peroxide (k(+2) = 2.17 x 10(3) s(-)(1)) is rate-limiting. The size and hydrophobicity of the o-diphenol substrates are correlated with their rate of binding to HRPC, while the electron density at the C-4 hydroxyl group predominantly influences the rate of electron transfer to the heme.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ascorbic Acid / chemistry
  • Benzothiazoles
  • Binding Sites
  • Horseradish Peroxidase / chemistry*
  • Horseradish Peroxidase / metabolism
  • Hydrogen Peroxide / chemistry
  • Indicators and Reagents
  • Kinetics
  • Models, Chemical
  • Nuclear Magnetic Resonance, Biomolecular
  • Oxidation-Reduction
  • Phenols / chemistry
  • Reducing Agents / chemistry
  • Substrate Specificity
  • Sulfonic Acids / chemistry

Substances

  • Benzothiazoles
  • Indicators and Reagents
  • Phenols
  • Reducing Agents
  • Sulfonic Acids
  • 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid
  • Hydrogen Peroxide
  • Horseradish Peroxidase
  • Ascorbic Acid