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Insights into the in Vitro and in Vivo SAR of Abscisic Acid – Exploring Unprecedented Variations of the Side Chain via Cross‐Coupling‐Mediated Syntheses
Author(s) -
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,
KoskullDöring Pascal,
Kleemann Jochen,
Lange Gudrun,
Lehr Stefan,
Müller Thomas,
Peschel Elisabeth,
Poree Fabien,
Schmutzler Dirk,
Schulz Arno,
Willms Lothar,
Wunschel Christian
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701687
Subject(s) - abscisic acid , chemistry , in vivo , sonogashira coupling , stille reaction , side chain , in vitro , alkyl , stereochemistry , biochemistry , organic chemistry , palladium , biology , microbiology and biotechnology , polymer , gene , catalysis
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.