Synthesis of the Methyl Ester of Tritium-labeled AK-toxin 1,a Host-specific Toxin Produced by Alternaria alternata Japanese Pear Pathotype

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  • OKADA Masakazu
    Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University
  • MIYAGAWA Hisashi
    Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University
  • UENO Tamio
    Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University

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タイトル別名
  • Synthesis of the Methyl Ester of Tritium-labeled AK-toxin I, a Host-specific Toxin Produced by Alternaria alternata Japanese Pear Pathotype.
  • Synthesis of the Methyl Ester of Tritium-labeled AK-toxin I, a Host-specific Toxin Produced by<i>Alternaria alternata</i>Japanese Pear Pathotype

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説明

AK-toxin I, a host-specific toxin to Japanese pear (Pyrus serotina), was synthesized as its methyl ester from three precursor fragments: conjugated diene-carboxylic acid, chiral epoxyalcohol and β-methylphenylalanine. The epoxyalcohol fragment was derived from D-fructose, in which effective homologation of the hemiacetal carbon to alkyne by using dimethyl 1-diazo-2-oxopropylphosphonate was the key reaction. The diene-carboxylic acid fragment was prepared by repeated Wittig reactions, and was combined with the epoxyalcohol fragment by the Stille reaction. Esterification of the combined product with the stereochemically-pure β-methylphenylalanine fragment afforded the target compound. This method was used to prepare the methyl ester of tritium-labeled AK-toxin I with a specific radioactivity of 213 GBq/mmol.<br>

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