56. ABA 8'-水酸化酵素のnon-azole阻害剤

概要

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Although some azole compounds inhibit ABA 8'-hydroxylase, their enzyme specificity is difficult to be estimated. An inhibitor having similar structure to ABA should be a specific inhibitor of ABA 8'-hydroxylase. Therefore, we designed and synthesized (1'S^*,2'S^*)-(±)-6-nor-2',3'-dihydro-4'-deoxo-ABA as a lead compound for the development specific inhibitor of the enzyme. The lead and ABA compound has similar affinity for the enzyme, although the lead has no ABA bioactivity. In the present study, we have tried to develop the stronger inhibitor than the lead by modification of C-8'. The new non-azole inhibitors, (1'S^*,2'S^*,6'S^*)-(±)-6-nor-2',3'-dihydro-4'-deoxo-8',8'-difluoro-ABA [(±)-1], (1'S^*,2'S^*,6'S^*)-(±)-6-nor-2',3'-dihydro-4'-deoxo-6'-hydroxy-8',9'-dinor-ABA [(±)-2] and (1'S^*,2'S^*)-(±)-6-nor-2',3'-dihydro-4'-deoxo-8',9'-cyolo-ABA [(±)-3] exhibited similar inhibition activity to the lead. Moreover, we found that (-)-1, witch is the unnatural type, is the stronger inhibitor than the natural type, (+)-1.
植物化学調節学会の論文
2005-10-13