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

Jens Frackenpohl; Erwin Grill; Guido Bojack; Rachel Baltz; Marco Busch; Jan Dittgen; Jana Franke; Jörg Freigang; Susana Gonzalez; Ines Heinemann; Hendrik Helmke; Martin Hills; Sabine Hohmann; Pascal von Koskull-Döring; Jochen Kleemann; Gudrun Lange; Stefan Lehr; Thomas Müller; Elisabeth Peschel; Fabien Poree; Dirk Schmutzler; Arno Schulz; Lothar Willms; Christian Wunschel

doi:10.1002/ejoc.201701687

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

Jens Frackenpohl, Erwin Grill, Guido Bojack, Rachel Baltz, Marco Busch, Jan Dittgen, Jana Franke, Jörg Freigang, Susana Gonzalez, Ines Heinemann, Hendrik Helmke, Martin Hills, Sabine Hohmann, Pascal von Koskull-Döring, Jochen Kleemann, Gudrun Lange, Stefan Lehr, Thomas Müller, Elisabeth Peschel, Fabien PoreeDirk Schmutzler, Arno Schulz, Lothar Willms, Christian Wunschel

Chair of Botany

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	1403-1415
Number of pages	13
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	12
DOIs	https://doi.org/10.1002/ejoc.201701687
State	Published - 29 Mar 2018

Keywords

Drought stress
Phytochemistry
Plant hormone
Stille coupling
Terpenoids

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10.1002/ejoc.201701687

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Frackenpohl, J., Grill, E., Bojack, G., Baltz, R., Busch, M., Dittgen, J., Franke, J., Freigang, J., Gonzalez, S., Heinemann, I., Helmke, H., Hills, M., Hohmann, S., von Koskull-Döring, P., Kleemann, J., Lange, G., Lehr, S., Müller, T., Peschel, E., ... Wunschel, C. (2018). Insights into the in Vitro and in Vivo SAR of Abscisic Acid – Exploring Unprecedented Variations of the Side Chain via Cross-Coupling-Mediated Syntheses. European Journal of Organic Chemistry, 2018(12), 1403-1415. https://doi.org/10.1002/ejoc.201701687

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title = "Insights into the in Vitro and in Vivo SAR of Abscisic Acid – Exploring Unprecedented Variations of the Side Chain via Cross-Coupling-Mediated Syntheses",

abstract = "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.",

keywords = "Drought stress, Phytochemistry, Plant hormone, Stille coupling, Terpenoids",

author = "Jens Frackenpohl and Erwin Grill and Guido Bojack and Rachel Baltz and Marco Busch and Jan Dittgen and Jana Franke and J{\"o}rg Freigang and Susana Gonzalez and Ines Heinemann and Hendrik Helmke and Martin Hills and Sabine Hohmann and {von Koskull-D{\"o}ring}, Pascal and Jochen Kleemann and Gudrun Lange and Stefan Lehr and Thomas M{\"u}ller and Elisabeth Peschel and Fabien Poree and Dirk Schmutzler and Arno Schulz and Lothar Willms and Christian Wunschel",

note = "Publisher Copyright: {\textcopyright} 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

month = mar,

day = "29",

doi = "10.1002/ejoc.201701687",

language = "English",

volume = "2018",

pages = "1403--1415",

journal = "European Journal of Organic Chemistry",

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Frackenpohl, J, Grill, E, Bojack, G, Baltz, R, Busch, M, Dittgen, J, Franke, J, Freigang, J, Gonzalez, S, Heinemann, I, Helmke, H, Hills, M, Hohmann, S, von Koskull-Döring, P, Kleemann, J, Lange, G, Lehr, S, Müller, T, Peschel, E, Poree, F, Schmutzler, D, Schulz, A, Willms, L & Wunschel, C 2018, 'Insights into the in Vitro and in Vivo SAR of Abscisic Acid – Exploring Unprecedented Variations of the Side Chain via Cross-Coupling-Mediated Syntheses', European Journal of Organic Chemistry, vol. 2018, no. 12, pp. 1403-1415. https://doi.org/10.1002/ejoc.201701687

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T1 - Insights into the in Vitro and in Vivo SAR of Abscisic Acid – Exploring Unprecedented Variations of the Side Chain via Cross-Coupling-Mediated Syntheses

AU - Frackenpohl, Jens

AU - Grill, Erwin

AU - Bojack, Guido

AU - Baltz, Rachel

AU - Busch, Marco

AU - Dittgen, Jan

AU - Franke, Jana

AU - Freigang, Jörg

AU - Gonzalez, Susana

AU - Heinemann, Ines

AU - Helmke, Hendrik

AU - Hills, Martin

AU - Hohmann, Sabine

AU - von Koskull-Döring, Pascal

AU - Kleemann, Jochen

AU - Lange, Gudrun

AU - Lehr, Stefan

AU - Müller, Thomas

AU - Peschel, Elisabeth

AU - Poree, Fabien

AU - Schmutzler, Dirk

AU - Schulz, Arno

AU - Willms, Lothar

AU - Wunschel, Christian

PY - 2018/3/29

Y1 - 2018/3/29

N2 - 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.

AB - 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.

KW - Drought stress

KW - Phytochemistry

KW - Plant hormone

KW - Stille coupling

KW - Terpenoids

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SN - 1434-193X

VL - 2018

SP - 1403

EP - 1415

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 12

ER -

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

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Keywords

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