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J. Biol. Chem., Vol. 262, Issue 32, 15354-15358, 11, 1987

Structure determination and biosynthesis of a novel metabolite of Fusarium culmorum, apotrichodiol

LO Zamir, KA Devor, Y Nadeau and F Sauriol
Universite du Quebec, Institut Armand-Frappier, Laval, Canada.

A novel dead-end metabolite of Fusarium culmorum was isolated and characterized (Zamir, L. O., and Devor, K. A. (1987) J. Biol. Chem. 15348-15353). This 3 alpha, 13-dihydroxy-apotrichothec-9-ene is herein given the trivial name of apotrichodiol to indicate its basic structure. The characterization of apotrichodiol was established through the application of spectroscopic techniques (ultraviolet, 1H- NMR, 13C-NMR, COSY, and DEPT experiments) on the natural product as well as on its diacetate derivative. The mode of folding of its precursor farnesyl pyrophosphate was derived from feeding experiments with 3,4-[13C2]mevalonolactone. 13C-NMR assignments were also made of 3- acetyldeoxynivalenol and sambucinol which were derived from these feedings with enriched mevalonolactone.
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