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Oxygen chiral phosphate esters.

J A Gerlt, J A Coderre, S Mehdi

    Advances in Enzymology and Related Areas of Molecular Biology
    |January 1, 1983
    PubMed
    Summary
    This summary is machine-generated.

    Stereochemical analysis of phosphate esters reveals insights into enzyme mechanisms. While most reactions suggest direct displacement or covalent intermediates, some phosphohydrolase reactions require further investigation.

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    Area of Science:

    • Biochemistry
    • Organic Chemistry
    • Enzymology

    Background:

    • Methods for synthesizing and analyzing chiral phosphate mono- and diesters using oxygen isotope substitution have advanced significantly.
    • These techniques have been applied to numerous enzymatic and chemical reactions.

    Purpose of the Study:

    • To review the application of stereochemical methods in understanding reaction mechanisms.
    • To evaluate the interpretation of configurational changes in enzymatic and chemical reactions involving phosphate esters.

    Main Methods:

    • Synthesis of chiral phosphate mono- and diesters via oxygen isotope substitution.
    • Configurational analysis of reaction products.
    • Application of these methods to enzymic and chemical reactions.

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    Main Results:

    • Stereochemical outcomes generally support simple interpretations: inversion suggests direct displacement, while retention implies a phosphorylated enzyme intermediate.
    • No experimental data currently contradicts these interpretations for most investigated reactions.
    • Potential complexities in phosphohydrolase reactions warrant further investigation regarding covalent catalysis.

    Conclusions:

    • The stereochemical approach is a powerful and direct method for determining if enzyme catalysis involves covalent intermediates.
    • While generally reliable, re-examination of specific reaction classes, like phosphohydrolases, is necessary to confirm mechanistic assignments.