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Biosynthesis of ketomycin.

Y Takeda, V Mak, C C Chang

    The Journal of Antibiotics
    |August 1, 1984
    PubMed
    Summary
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    Ketomycin biosynthesis involves shikimic acid, chorismic acid, and prephenic acid. Prephenic acid

    Area of Science:

    • Biochemistry
    • Natural Product Biosynthesis
    • Organic Chemistry

    Background:

    • Ketomycin is an antibiotic with a complex biosynthetic pathway.
    • Understanding the precise steps and intermediates is crucial for antibiotic research.
    • Shikimic acid is a key precursor in many natural product syntheses.

    Purpose of the Study:

    • To elucidate the biosynthetic pathway of the antibiotic ketomycin.
    • To identify the specific intermediates involved in ketomycin formation.
    • To investigate the stereochemical aspects of prephenic acid conversion to ketomycin.

    Main Methods:

    • Utilized [1,6-14C]shikimic acid as a labeled precursor.
    • Analyzed ketomycin degradation products.
    • Investigated the stereospecificity of enzymatic reactions.

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    Main Results:

    • Confirmed shikimic acid, chorismic acid, and prephenic acid as intermediates.
    • Ruled out phenylalanine and 2',5'-dihydrophenylalanine as intermediates.
    • Demonstrated stereospecific conversion of prephenic acid to ketomycin, with the pro-S-R edge forming the C-2', C-3' side.

    Conclusions:

    • The biosynthetic pathway of ketomycin proceeds through prephenic acid.
    • The conversion of prephenic acid is highly stereospecific.
    • This study clarifies key steps in ketomycin antibiotic biosynthesis.