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Cysteine adds to liquid hydroperoxide

H W Gardner, R Kleiman, D Weisleder

    Lipids
    |August 1, 1977
    PubMed
    Summary
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    Cysteine reacts with linoleic acid hydroperoxide, forming fatty acid-cysteine adducts. Ferric chloride catalysis initiates free radical reactions, yielding specific hydroxy and ethoxy adducts, and a 9-oxononanoic acid adduct.

    Area of Science:

    • Biochemistry
    • Organic Chemistry
    • Free Radical Chemistry

    Background:

    • Linoleic acid hydroperoxides are reactive species involved in lipid peroxidation.
    • Cysteine is a sulfur-containing amino acid with nucleophilic properties.
    • Understanding adduct formation is crucial for studying oxidative stress and biomolecule modification.

    Purpose of the Study:

    • To investigate the reaction products between cysteine and linoleic acid hydroperoxide.
    • To identify the structures of fatty acid-cysteine adducts formed.
    • To elucidate the reaction mechanisms, including the role of ferric chloride and free radicals.

    Main Methods:

    • Reaction of cysteine with isomerically pure and mixed linoleic acid hydroperoxides.
    • Catalysis by ferric chloride under nitrogen and air.

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  • Isolation and identification of reaction products using analytical techniques.

    • Main Results:

    • Formation of several fatty acid-cysteine adducts.
    • Identification of 9-S-cysteine-13-hydroxy-10-ethoxy-trans-11-octadecenoic acid (I) and 9-S-cysteine-10,13-dihydroxy-trans-11-octadecenoic acid (II) as major adducts.
    • Isolation of a 9-oxononanoic acid-cysteine adduct under different reaction conditions.

    Conclusions:

    • Cysteine readily reacts with linoleic acid hydroperoxide to form adducts.
    • Ferric chloride catalyzes the reaction via free radical pathways.
    • The study identified specific adduct structures and provided insights into their formation mechanisms.