Phytochemistry p. 1251 - 1258 (1996)
Update date:2022-07-31
Topics:
Rose, Patricia A.
Lei, Bo
Shaw, Angela C.
Barton, Dennis L.
Walker-Simmons
Abrams, Suzanne R.
(+)-(S)- and (-)-(R)-C-1′-O-methyl abscisic acids and their methyl esters, as well as the methyl ethers of the acetylenic analogue of methyl ABA, were synthesized through an enantioselective route, giving a series of optically active, new C-1′ substituted analogues with known stereochemistry. In a wheat embryo germination inhibition assay, (-)-C-1′-O-methyl ABA shows high activity, comparable with (+)- and (-)-ABA, whereas (+)-C-1′-O-methyl ABA is less active. In a wheat seedling transpiration assay, both analogues exhibit weak activity although the (+)-ABA-like analogue is more potent than its enantiomer. The anti-transpirant response increases over time, which may indicate that the analogue is being metabolized to ABA in vivo. Copyright
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(1996)