95(P14) シクロプロパンアナログによるアブシジン酸の活性コンホメーション解析(ポスター発表の部)

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Abscisic acid [(I'S)-(+)-ABA, 1] is the plant hormone inducing physiological responses to the environmental stresses such as drought and freezing. Revealing structural requirements for the ABA activity is essential to developing the highly active analogues and photoaffinity probes for the active site on the receptor. The favored conformation of the ring in ABA is believed to be a half-chair with the side chain in the pseudo-axial orientation. However, the ring is flexible, so the conformation of ABA can change into another one in binding to the ABA receptor. For investigating ring conformational requirement for the biological activity of abscisic acid, the cyclopropane analogues 2, 3, 5, and 6 were synthesized and their biological activities in four bioassays were tested. The activity of the achiral cyclohexadienone analogue 4 also was examined. Analogue 3 in which the 6'β-substituent is constrained essentially to the axial-like orientation between axial and bisectional showed no activity, while 2 and 4 with no axial-like substituent at C-6'β independent of the conformational preference exhibited the equivalent activity to abscisic acid. This result suggested that the axial substituent at the β-side of the ring is fatal to the activity. The active conformation of abscisic acid would be a conformation where C-9' is equatorial and the side chain is between pseudo-axial and bisectional, that is, close to the favored half-chair with the side chain pseudo-axial rather than the less favored half-chair with the side chain pseudo-equatorial.
天然有機化合物討論会の論文
1996-09-02

95(P14) シクロプロパンアナログによるアブシジン酸の活性コンホメーション解析(ポスター発表の部)

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