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A Detailed View of 2-Methylisoborneol Biosynthesis

Authors

  • Nelson L. Brock,

    1. Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig (Germany)
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  • Srinivasa R. Ravella,

    1. Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig (Germany)
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  • Prof. Dr. Stefan Schulz,

    Corresponding author
    1. Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig (Germany)
    • Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig (Germany)
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  • Dr. Jeroen S. Dickschat

    Corresponding author
    1. Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig (Germany)
    • Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig (Germany)
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  • Funding by the Deutsche Forschungsgemeinschaft with an Emmy-Noether Fellowship (to J.S.D., DI1536/1-2) and a grant “Duftstoffe aus Actinomyceten” (DI1536/2-1), and by the Fonds der Chemischen Industrie with a Chemiefonds scholarship (to N.L.B.) is gratefully acknowledged. We thank Bertolt Gust and Lutz Heide (Tübingen) for the strain S. lividans TK 24, Hans-Peter Fiedler (Tübingen) for the strain S. violaceusniger Tü 4113, and the US Department of Agriculture for the strain S. scabiei 87.22.

Abstract

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Odor of earth: Several homomonoterpenes were identified in actinomycetes that produce 2-methylisoborneol (2-MIB, see scheme, which is responsible for an earthy odor in drinking water). Their occurrence clarifies the 2-MIB pathway, because they are derived from cationic intermediates that are otherwise difficult to detect. A highly sensitive method using feeding experiments with 13C-labeled precursors gives detailed insights into 2-MIB biosynthesis.

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