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Related Experiment Videos

Rate acceleration by stereopopulation control: models for enzyme action.

S Milstien, L A Cohen

    Proceedings of the National Academy of Sciences of the United States of America
    |November 1, 1970
    PubMed
    Summary
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    Alkyl substitution dramatically accelerates acid-catalyzed lactonization of hydrocoumaric acid, by factors up to 10^16. This conformational restriction effect serves as an enzyme catalysis model.

    Area of Science:

    • Organic Chemistry
    • Biochemistry
    • Chemical Kinetics

    Background:

    • Acid-catalyzed lactonization is a key reaction in organic synthesis.
    • Enzyme catalysis significantly enhances reaction rates through various mechanisms.
    • Understanding substrate conformational effects is crucial for enzyme mechanism elucidation.

    Purpose of the Study:

    • To investigate the impact of alkyl substitution on hydrocoumaric acid lactonization rates.
    • To explore the role of conformational restriction in accelerating chemical reactions.
    • To model enzyme-substrate interactions using a synthetic system.

    Main Methods:

    • Studied acid-catalyzed lactonization of hydrocoumaric acid derivatives.
    • Varied alkyl substitution on aromatic ring and side chain.

    Related Experiment Videos

  • Measured reaction rate constants and half-lives under specific buffer conditions (pH 7, 30°C).

    • Main Results:

    • Alkyl substitution increased lactonization rate constants by up to 10^11.
    • Compared to phenol esterification, rates increased by nearly 10^16.
    • A specific phenolic acid derivative showed a half-life of 6 seconds, with 90% buffer catalysis.
    • Conformational restriction due to interlocking methyl groups was identified as the cause.

    Conclusions:

    • Severe conformational restriction of the side chain significantly enhances reaction rates.
    • This phenomenon provides a model for enzyme-induced substrate conformational restraint.
    • Substrate 'freezing' may contribute substantially to enzyme catalysis, potentially justifying the entire rate enhancement.