Generation and characterization of halogenated compounds in hairy roots of Brassica by transformation with bacterial halogenases
The introduction of a halogen into a natural product has frequently been demonstrated to improve bioactivity and bioavailability. Furthermore, the incorporation of chlorine or bromine into a natural product provides a reactive handle that may be utilised for further site-specific functionalisation. Using flavin-dependent halogenases regioselective incorporation of halogen atoms can be achieved. Flavin-dependent halogenases are two-component systems consisting of a flavin reductase producing FADH2 and the halogenase. The huge advantage of these halogenases over chemical halogenation is that they have 100% regioselectivity and thus produce no unwanted by-products. Tryptophan halogenases are especially suited for this purpose since they use free tryptophan as the substrate. Already available tryptophan halogenases and variants from the project will be used to transform plants producing tryptophan-containing secondary metabolites or indole derivatives to obtain new halogenated compounds produced in vivo. We have chosen a plant species with a highly diverse range of indole derived metabolites to analyze furthermore their bioactive potential. A collaborative project with Karl-Heinz van Pee (TU Dresden), Sarah O'Connor (John Innes Centre), Rebecca Goss (University of St. Andrews), Alfredo Aires (Universidade de Tras-os-Montes e Alto Douro), Vita34 AG (Bioplanta Leipzig).
Publications:
- Aires, A., Neumann, M., Ludwig-Müller, J., Schöpe, M., van Pée, K.H. (2019). Induced production of indol-3-ylmethyl glucosinolates in hairy roots of Chinese cabbage (Brassica rapa subsp. pekinensis): perspectives to enhance the content of bioactive compounds. Acta Hortic. 1242: 49-56
- Neumann, M., Prahl, S., Caputi, L., Hill, L., Kular, B., Walter, A., Patallo, E., Milbredt, D., Aires, A., Schöpe, M., O'Connor, S., van Pée, K.-H., Ludwig-Müller, J. (2020) Hairy root transformation of Brassica rapa with bacterial halogenase genes and regeneration to adult plants to modify production of indolic compounds. Phytochemistry 175: 112371
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