83149-61-5Relevant academic research and scientific papers
The Metabolism of (2Z.4E)-α-Ionylideneacetic Acid in Cercospora cruenta, a Fungus Producing (+)-Abscisic Acid
Ichimura, Michio,Oritani, Takayuki,Yamashita, Kyohei
, p. 1895 - 1900 (2007/10/02)
(+/-)-(2Z,4E)-α-Ionylideneacetic acid (2) was enantioselectively oxidized to (-)-(1'S)-(2Z,4E)-4'-hydroxy-α-ionylideneacetic acid (3), (+)-(1'R)-(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-(14)C)-(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 α-acid (+)-2 and (-)-2, as the substrates.
