8',8'-Difluoro- and 8',8',8'-trifluoroabscisic acids as highly potent, long-lasting analogues of abscisic acid
1995
Todoroki, Y. | Hirai, N. | Koshimizu, K.
Racemic 8',8'-difluoroabscisic acid (difluoro-ABA) and 8',8',8'-trifluoroabscisic acid (trifluoro-ABA) were synthesized as highly potent, long-lasting analogues of abscisic acid (ABA). The individual optical isomers were obtained by optical resolution of the racemic mixture by HPLC with a chiral column. (+)-8',8'-Difluoro-ABA and (+)-8',8',8'-trifluoro-ABA inhibited the elongation of rice seedlings six and 30 times more strongly, respectively, than (+)-ABA. These analogues also showed double the (+)-ABA-induced inhibition of lettuce seed germination. In causing stomatal closure and inhibiting the induction of alpha-amylase by gibberellin A3, these analogues were equally as effective as (+)-ABA. The high activity in the assays over a long period suggested that the metabolism of difluoro- and trifluoro-ABAs was delayed. (-)-Enantiomers were equal to, or weaker than (-)-ABA in the assays.
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