Achiral cyclohexadienone analogues of abscisic acid: Synthesis and biological activity

Lei, Bo; Abrams, Suzanne R.; Ewan, Bruce; Gusta, L. V.

doi:10.1016/0031-9422(94)85049-6

Cited by 22 publications

(16 citation statements)

References 17 publications

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“…Such information was not obtained from (+ )-alkyl-ABAs, since (+ )-ABA cannot have a substituent which occupies this space. Lei et al have recently reported that the methyl ester of a symmetric cyclohexadienone analogue (28) of ABA was as active as ( + )-ABA in inhibiting the root emergence of cress seeds, 12) also supporting the hypothesis of pseudo-symmetry for ABA.…”

Section: Biological Activitymentioning

confidence: 87%

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Synthesis and Biological Activity of 7′-, 8′-, and 9′-Alkyl Analogues of Abscisic Acid

Nakano¹,

Todoroki²,

Hirai³

et al. 1995

Bioscience, Biotechnology, and Biochemistry

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Section: Biological Activitymentioning

confidence: 87%

“…1 (2), 126 (6), 112 (6), 96 (5), 82 (100). (12). To a stirred solution of I-methyl-2-propynyl THP ether (53 g) in THF (420 ml) was added dropwise n-butyl lithium (a 1.6 M solution in hexane, 220 ml) during 1.5 h at -78°C under nitrogen.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Biological Activity of 7′-, 8′-, and 9′-Alkyl Analogues of Abscisic Acid

Nakano¹,

Todoroki²,

Hirai³

et al. 1995

Bioscience, Biotechnology, and Biochemistry

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“…12) The conjugate addition of trideuteromethylmagnesium iodide 13 ) to C-6' in the presence of copper(I) iodide proceeded diastereoselectively to give only one isomer d 3 -1a in a 34% yield (Fig. 2) diastereoselective reaction may have occurred with coordination of the C-l' hydroxyl oxygen and the C-4' carbonyl oxygen with magnesium to produce an intermediate complex, in which the side of the C-l' hydroxyl group was more readily accessible for a methylation reagent than the other side (Fig.…”

Section: Diastereoselective Synthesismentioning

confidence: 97%

Synthesis, Biological Activity, and Metabolism of 8′,8′,8′-Trideuteroabscisic Acid

Todoroki

Nakano

Hirai

et al. 1997

Bioscience, Biotechnology, and Biochemistry

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An 8',8',8'-trideuterated analog of abscisic acid (ABA) was diastereoselectively synthesized as a new analog of ABA that is resistant to 8'-hydroxyIation, the first metabolic reaction of ABA, owing to the primary kinetic isotope effect. (+)-8',8',8'-Trideutero-ABA showed long-term activity in the rice elongation assay. The rate of metabolism of this analog in rice cell suspension culture was about two fold slower than that of (+)-ABA. The concentration of 8',8'-dideuterophaseic acid produced was about 1/3 that of phaseic acid converted from (+)-ABA. This result indicated that the long-lasting activity of the (+)-trideutero-ABA in the rice assay was the result of the delayed 8'-hydroxylation as expected.

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“…j-Methyl 8'-Methylene Abscisate Methyl (22, 4E)-5-(2,6-dimethyl-1-hydroxy-4-oxocyclohexa-2,5-dienyl)-3-methylpent-2,4-dienoate (3.60 g, 13.7 mmol; Lei et al, 1994) was dissolved in dry THF (300 mL) and cooled to -78°C with an externa1 dry icelacetone bath. Methyllithium (Aldrich; 1.4 M in THF, 9.7 mL, 13.7 mmol) was added and the solution was stirred for 15 min.…”

Section: General Experimental Conditionsmentioning

confidence: 99%

8[prime]-Methylene Abscisic Acid (An Effective and Persistent Analog of Abscisic Acid)

et al. 1997

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l h e alteration in the ABA structure causes the analog to be metabolized more slowly than ABA, resulting in longer-lasting and more effective biological activity relative to ABA.The plant hormone (+)-ABA ( Fig. 1) regulates diverse aspects of plant growth, including development and germination of seeds, transpiration, and adaptive responses to environmental stresses (Zeevaart and Creelman, 1988;Davies and Jones, 1991). Considerable progress has been made in the identification of ABA-responsive genes, mutant characterization, and signaling (Bray, 1993;Chandler and Robertson, 1994;Giraudat et al., 1994). However, examination of the mechanisms of ABA action, identification of receptor proteins, and cellular localization of the hormone have been restricted by the rapid turnover of ABA in plants. Similarly, agricultura1 uses of applied ABA have been limited by its rapid metabolism in plants. Thus, the aim of the current research was to develop potent biologically stable ABA analogs that can be used to prolong ABA-like effects in plants for agricultural and basic research applications.Biologically stable analogs of other plant hormones, especially of the auxins, have proven to be useful tools for This is National Research Council of Canada paper no. 40712.

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Achiral cyclohexadienone analogues of abscisic acid: Synthesis and biological activity

Cited by 22 publications

References 17 publications

Synthesis and Biological Activity of 7′-, 8′-, and 9′-Alkyl Analogues of Abscisic Acid

Synthesis and Biological Activity of 7′-, 8′-, and 9′-Alkyl Analogues of Abscisic Acid

Synthesis, Biological Activity, and Metabolism of 8′,8′,8′-Trideuteroabscisic Acid

8[prime]-Methylene Abscisic Acid (An Effective and Persistent Analog of Abscisic Acid)

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