4.5 Article

Effect of the minor ABA metabolite 7′-hydroxy-ABA on Arabidopsis ABA 8′-hydroxylase CYP707A3

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BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
卷 17, 期 17, 页码 4977-4981

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PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2007.06.018

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abscisic acid; ABA; 7'-Hydroxy-ABA; cytochrome p450; ABA 8'-hydroxylase

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To examine the effect of the minor abscisic acid (ABA) metabolite 7'-hydroxy-ABA on Arabidopsis ABA W-hydroxylase (CYP707A3), we developed a novel and facile, four-step synthesis of 7'-hydroxy-ABA from alpha-ionone. Structural analogues of Thydroxy-ABA, 1'-deoxy-7'-hydroxy-ABA, and 7'-oxo-ABA were also synthesized to evaluate the role of the T-hydroxyl group on binding to the enzyme. The result of enzyme inhibition assay suggests that the local polarity at C-T, neither steric bulkiness nor overall molecular hydrophilicity, would be the major reason why (+)-7'-hydroxy-ABA is not a potent inhibitor of CYP707A3. (C) 2007 Elsevier Ltd. All rights reserved.

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