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Compound X. An intermediate in enzymatic halogenation.

R Chiang, T Rand-Meir, R Makino

    The Journal of Biological Chemistry
    |October 25, 1976
    PubMed
    Summary
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    Horseradish peroxidase uses chlorite as a halogen donor. A new intermediate, Compound X, is formed rapidly at acidic pH and is the key halogenating species in this enzymatic chlorination reaction.

    Area of Science:

    • Biochemistry
    • Enzymology

    Background:

    • Chlorite is known to act as a halogenation substrate for horseradish peroxidase (HRP).
    • In this role, chlorite functions as both a halogen donor and an oxidant for chlorination reactions.

    Purpose of the Study:

    • To identify and characterize the initial spectral intermediate formed during the reaction of chlorite with HRP.
    • To elucidate the role of this intermediate in the overall enzymatic chlorination process.

    Main Methods:

    • Spectroscopic detection of reaction intermediates.
    • Kinetic analysis of intermediate formation and decay.
    • pH-dependent rate measurements.

    Main Results:

    • A novel spectral intermediate, designated Compound X, was identified as the initial product of the chlorite-HRP reaction.

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  • Compound X formation is rapid, particularly at acidic pH, with a second-order rate constant (Kf) of 0.9 x 10^6 M^-1 s^-1 at pH 4.5.
  • Compound X decomposes to Compound I and chloride ion with a first-order rate constant (Kd) of 0.2 s^-1 at pH 4.5.
  • The pH optimum for enzymatic chlorination aligns with the pH profile of Compound X's stability (Kf/Kd).

    • Conclusions:

    • Compound X is the principal halogenating intermediate in the HRP-chlorite reaction.
    • The rate of enzymatic chlorination is directly proportional to the stability of Compound X.
    • A proposed structure for Compound X is an -OCl ligand on a ferric heme.