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Probing the role of the hydroxyl group of ABA: Analogues with a methyl ether AT C-1'

From National Research Council Canada

DOIResolve DOI: https://doi.org/10.1016/0031-9422(95)00781-4
AuthorSearch for: 1; Search for: 1; Search for: 1; Search for: 1; Search for: ; Search for: 1
Affiliation
  1. National Research Council of Canada. NRC Plant Biotechnology Institute
FormatText, Article
SubjectTriticum aestivum L.; Gramineac; Clark's cream; Katepwa; wheat; abscisic acid analogues; antitranspirant; germination inhibition; C-1'; methyl ether; acetylenic analogues
Abstract
(+)-(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.
Publication date
PublisherElsevier
In
  • Phytochemistry 41, no. 5 (March 1996): 1251–1258.
LanguageEnglish
Peer reviewedYes
Identifier0031942295007814
NRCC-38933
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Record created2023-11-02
Record modified2023-11-02
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