The Metabolism of (2Z, 4Z)-α-Ionylideneacetic Acid in Cercospora cruenta, a Fungus Producing (+)-Abscisic Acid

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概要

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• (±)-(2Z, 4E)-α-Ionylideneacetic acid (2) was enantioselectively oxidized to (-)-(1S)-(2Z, 4E)- 4-hydroxy-α-ionylideneacetic acid (3), (+)-(1R)-(2Z, 4E)-4-oxo-α-ionylideneacetic acid (4) and (+)-abscisic acid (ABA) (1) by Cercospora cruenta IFO 6164, which can produce (+)-ABA and (+)-4-oxo-α-acid 4. This metabolism was confirmed by the incorporation of radioactivity from (±)-(2-14C)-(2Z, 4E)-α-acid 2 into three metabolites. (-)-4-Hydroxy-α-acid 3 was a diastereoisomeric mixture consisting of major 1, 4-trans-4-hydroxy-α-acid 3a and minor 1, 4-cis-4-hydroxy-α-acid 3b. These structures, 3a and 3b, were confirmed by 13C-NMR and 1H-NMR analysis. Also, the enantioselectivity of the microbial oxidation was reexamined by using optically pure aacid (+)-2 and (-)-2, as the substrates.

• 社団法人 日本農芸化学会の論文

著者

• Ichimura Michio

  Department Of Biochemistry Vanderbilt University School Of Medicine

• Yamashita Kyohei

  Department Of Agricultural Chemistry Faculty Of Agriculture Tohoku University

• Oritani Takayuki

  Department Of Agricultural Chemistry Faculty Of Agriculture Tohoku University

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