Insights into the in Vitro and in Vivo SAR of Abscisic Acid – Exploring Unprecedented Variations of the Side Chain via Cross‐Coupling‐Mediated Syntheses

Novel analogues of the plant hormone abscisic acid (ABA) were designed and prepared to explore the impact that modifications of its terpenoid side chain have on receptor affinity and in vivo efficacy against drought stress in selected crops. Their efficient and versatile synthesis proceeded via Stil...

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Published in:European journal of organic chemistry 2018-03, Vol.2018 (12), p.1403-1415
Main Authors: Frackenpohl, Jens, Grill, Erwin, Bojack, Guido, Baltz, Rachel, Busch, Marco, Dittgen, Jan, Franke, Jana, Freigang, Jörg, Gonzalez, Susana, Heinemann, Ines, Helmke, Hendrik, Hills, Martin, Hohmann, Sabine, Koskull‐Döring, Pascal, Kleemann, Jochen, Lange, Gudrun, Lehr, Stefan, Müller, Thomas, Peschel, Elisabeth, Poree, Fabien, Schmutzler, Dirk, Schulz, Arno, Willms, Lothar, Wunschel, Christian
Format: Article
Language:English
Subjects:
Abscisic acid
Chains
Coupling (molecular)
Couplings
Crops
Crystallography
Drought
Drought stress
Phytochemistry
Plant hormone
Stille coupling
Terpenoids
Wheat
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Summary:Novel analogues of the plant hormone abscisic acid (ABA) were designed and prepared to explore the impact that modifications of its terpenoid side chain have on receptor affinity and in vivo efficacy against drought stress in selected crops. Their efficient and versatile synthesis proceeded via Stille or Sonogashira couplings, shortening the synthetic route significantly. In line with molecular modelling and X‐ray crystallography studies novel ABA‐derivatives with small alkyl, cycloalkyl or haloalkyl substituents showed strong effects in vitro and in vivo against drought stress in crops, particularly canola and wheat. Herein, we disclose a series of novel abscisic acid derivatives exhibiting strong effects in vitro and in vivo against drought stress in crops, particularly canola and wheat. Promising effects were also observed in corn and barley. Our combined in vivo/in vitro structure‐activity relationship (SAR) study is corroborated by results from crystal structure analyses and receptor specificity tests.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201701687