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Open AccessArticle

Chlorinated Auxins—How Does Arabidopsis Thaliana Deal with Them?

1
Institute of Botany, Technische Universität Dresden, 01062 Dresden, Germany
2
Department of Natural Product Synthesis, Max Planck Institute for Chemical Ecology, 07745 Jena, Germany
3
Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2020, 21(7), 2567; https://doi.org/10.3390/ijms21072567
Received: 25 March 2020 / Accepted: 3 April 2020 / Published: 7 April 2020
Plant hormones have various functions in plants and play crucial roles in all developmental and differentiation stages. Auxins constitute one of the most important groups with the major representative indole-3-acetic acid (IAA). A halogenated derivate of IAA, 4-chloro-indole-3-acetic acid (4-Cl-IAA), has previously been identified in Pisum sativum and other legumes. While the enzymes responsible for the halogenation of compounds in bacteria and fungi are well studied, the metabolic pathways leading to the production of 4-Cl-IAA in plants, especially the halogenating reaction, are still unknown. Therefore, bacterial flavin-dependent tryptophan-halogenase genes were transformed into the model organism Arabidopsis thaliana. The type of chlorinated indole derivatives that could be expected was determined by incubating wild type A. thaliana with different Cl-tryptophan derivatives. We showed that, in addition to chlorinated IAA, chlorinated IAA conjugates were synthesized. Concomitantly, we found that an auxin conjugate synthetase (GH3.3 protein) from A. thaliana was able to convert chlorinated IAAs to amino acid conjugates in vitro. In addition, we showed that the production of halogenated tryptophan (Trp), indole-3-acetonitrile (IAN) and IAA is possible in transgenic A. thaliana in planta with the help of the bacterial halogenating enzymes. Furthermore, it was investigated if there is an effect (i) of exogenously applied Cl-IAA and Cl-Trp and (ii) of endogenously chlorinated substances on the growth phenotype of the plants. View Full-Text
Keywords: Arabidopsis thaliana; auxin; bacterial halogenase; chloro-tryptophan, chloro-indole acetic acid, chloro-indole acetonitrile, plant natural products, plant metabolic engineering Arabidopsis thaliana; auxin; bacterial halogenase; chloro-tryptophan, chloro-indole acetic acid, chloro-indole acetonitrile, plant natural products, plant metabolic engineering
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Walter, A.; Caputi, L.; O’Connor, S.; van Pée, K.-H.; Ludwig-Müller, J. Chlorinated Auxins—How Does Arabidopsis Thaliana Deal with Them? Int. J. Mol. Sci. 2020, 21, 2567.

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