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  Strategies to produce chlorinated indole-3-acetic acid and indole-3-acetic acid intermediates

Patallo, E. P., Walter, A., Milbredt, D., Thomas, M., Neumann, M., Caputi, L., et al. (2017). Strategies to produce chlorinated indole-3-acetic acid and indole-3-acetic acid intermediates. ChemistrySelect, 2(34), 11148-11153. doi:10.1002/slct.201701933.

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Patallo, Eugenio P., Author
Walter, Antje, Author
Milbredt, Daniela, Author
Thomas, Marion, Author
Neumann, Madeleine, Author
Caputi, Lorenzo1, Author              
O'Connor, Sarah E.1, Author              
Ludwog-Müller, Jutta, Author
van Pée, Karl-Heinz, Author
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1External Organizations, ou_persistent22              

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 Abstract: Tryptophan and indole derivatives are common precursors in many natural biosynthetic pathways. In recent years it has been shown that the substrate specificity of tryptophan halogenases is much more relaxed than previously thought. Using the tryptophan 7-halogenase PrnA, the tryptophan 6-halogenase ThdH, and the tryptophan 5-halogenase PyrH we achieved the regioselective mono-halogenation of indole-3-acetic acid (IAA), which has not been reported as a substrate of tryptophan halogenases to date. The tryptophan 5-halogenase gene was introduced into Arabidopsis thaliana leading to the formation of 5-chlorotryptophan, 5-chloroindole-3-acetonitrile and 5- chloro-3-indole acetic acid by A. thaliana. PyrH activity could also be demonstrated for the plant-produced halogenase in vitro. These results show the potential of flavin-dependent halogenases to generate novel halogenated auxins or other secondary metabolites in vitro and in vivo by plants.

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 Dates: 2017-11-172017
 Publication Status: Published in print
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 Identifiers: Other: SOC083
DOI: 10.1002/slct.201701933
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Title: ChemistrySelect
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 2 (34) Sequence Number: - Start / End Page: 11148 - 11153 Identifier: ISSN: 2365-6549
CoNE: https://pure.mpg.de/cone/journals/resource/2365-6549