Synthesis, Biological Activity, and Metabolism of 8′,8′,8′-Trideuteroabscisic Acid

Article abstract of DOI:10.1271/bbb.61.1872

An 8′,8′,8′-trideuterated analog of abscisic acid (ABA) was diastereoselectively synthesized as a new analog of ABA that is resistant to 8′-hydroxylation, the first metabolic reaction of ABA, owing to the primary kinetic isotope effect. (+)-8′,8′,8′-Trideutero-ABA showed long-term activity in the rice elongation assay. The rate of metabolism of this analog in rice cell suspension culture was about two fold slower than that of (+)-ABA. The concentration of 8′,8′-dideuterophaseic acid produced was about 1/3 that of phaseic acid converted from (+)-ABA. This result indicated that the long-lasting activity of the (+)-trideutero-ABA in the rice assay was the result of the delayed 8′-hydroxylation as expected.

Full text of DOI:10.1271/bbb.61.1872

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Synthesis, Biological Activity, and Metabolism of
8′,8′,8′-Trideuteroabscisic Acid
Yasushi Todorokia, Sei-ichi Nakanoa, Nobuhiro Hiraia, Toshiaki Mitsuiab & Hajime Ohigashia
a Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University,
Kitashirakawa-oiwake-cho, Sakyo-ku, Kyoto 606–01, Japan
b Department of Applied Biological Chemistry, Faculty of Agriculture, Niigata University,
2–8050 Ikarashi, Niigata 950–21, Japan
Published online: 12 Jun 2014.
To cite this article: Yasushi Todoroki, Sei-ichi Nakano, Nobuhiro Hirai, Toshiaki Mitsui & Hajime Ohigashi (1997) Synthesis,
Biological Activity, and Metabolism of 8′,8′,8′-Trideuteroabscisic Acid, Bioscience, Biotechnology, and Biochemistry,
61:11, 1872-1876, DOI: 10.1271/bbb.61.1872
To link to this article: http://dx.doi.org/10.1271/bbb.61.1872
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