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Journal Article

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

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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.

Cite as: https://hdl.handle.net/21.11116/0000-0002-DADE-F
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.