A new non-azole inhibitor of ABA 8′-hydroxylase: effect of the hydroxyl group substituted for geminal methyl groups in the six-membered ring

Y Araki, A Miyawaki, T Miyashita, M Mizutani…

Index: Araki, Yoshiharu; Miyawaki, Arisa; Miyashita, Tomoyuki; Mizutani, Masaharu; Hirai, Nobuhiro; Todoroki, Yasushi Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 12 p. 3302 - 3305

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Citation Number: 13

Abstract

We designed and synthesized AHI4 that has an axial hydroxyl group instead of geminal methyl groups at C-6′ of AHI1, previously reported as a lead compound for the development of non-azole inhibitors of ABA 8′-hydroxylase.(+)-AHI4 competitively inhibited 8′-hydroxylation of ABA by recombinant CYP707A3. The KI value was found to be 0.14 μM, 10-fold less than that of (+)-AHI1, suggesting that enzyme affinity increased by a factor of ...