Enzymatic Incorporation of Halogen Atoms into Natural Compounds

Kling, E.; Schmid, Christoph; Unversucht, S.; Wage, Tobias; Zehner, Susanne; Pée, K.-H. Van

doi:10.1007/3-540-27055-8_8

Cited by 15 publications

(22 citation statements)

References 56 publications

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“…Pseudomonas fluorescens BL915 ∆ORF1-4 pCIBhisprnA (prnA strain), 15 P. fluorescens BL915 ∆ORF1-4 pCIBhisprnB (prnB strain), 15 P. fluorescens BL915 ∆ORF1 pCIBhisthal (thal strain), 16 P. chlororaphis ACN pCIBhisthal, 16 and P. fluorescens BL915 ∆ORF1 pSZexM2 (pyrH strain) 17 have been generated by van Pée's group at the Biochemical Institute of Technische Universität Dresden. P. fluorescens strains were grown at 30 ℃ on modified LB 18 supplemented with 50 µg/mL kanamycin and 30 µg/mL tetracycline, if necessary, for 2 d.…”

Section: Bacterial Strains Culture Conditionsmentioning

confidence: 99%

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Flavin‐dependent Tryptophan Halogenases and Their Use in Formation of Novel Tryptophan Derived Compounds

2008

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Flavin-dependent halogenases are now known to play a significant role in the introduction of chloride and bromide into activated organic molecules. Herein a new strategy was reported to formate monodechloroaminopyrrolnitrin derivative 3-(2-amino-4-chlorophenyl)pyrrole, which is a key intermediate for the analysis and mutagenesis of pyrrolnitrin biosynthesis, by combinatorial biosynthesis using regioselective tryptophan halogenases. The successful production in Pseudomonas, with combinatorial cultivating method, demonstrates the feasibility of the new approach to modify and analyze these important secondary metabolite pathways.

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Section: Bacterial Strains Culture Conditionsmentioning

confidence: 99%

“…The purified enzyme was stored at -20 ℃. 16,17 Isolation and purification of monodechloroaminopyrrolnitrin and 3-(2-amino-4-chlorophenyl)pyrrole prnA strain and thal strain were precultured in 6×1 L of HNB medium supplemented with antibiotics at 30 ℃ and 150 r/min, respectively.…”

Section: Purification Of Enzyme By Ni-chelating Affinity Chromatographymentioning

confidence: 99%

Flavin‐dependent Tryptophan Halogenases and Their Use in Formation of Novel Tryptophan Derived Compounds

2008

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Section: Introductionmentioning

confidence: 98%

“…Halogenating enzymes are mainly grouped into two classes: haloperoxidases (HPO) and halogenases (Kling et al, 2005). HPOs were shown to be less specific, whereas halogenases could be demonstrated to be highly substrate specific (Kling et al, 2005;van Pee and Patallo, 2006). More recently, the group of a-ketoglutarate-O 2 -dependent halogenases were shown to be involved in the biosynthesis of halogen incorporation in aliphatic moieties, as in syringomycin E or barbamide ( Fig.…”

Section: Introductionmentioning

confidence: 98%

“…1), for which antimicrobial activities have been reported (Falch et al, 1993;Wright et al, 2005). A precise understanding of biological halogenation will give rise to new enzymatic methods for generating halogenated analogues of biologically active compounds, which might have altered bioactivities (Hofrichter and Ullrich, 2006;Kling et al, 2005;Murphy, 2006; van Pee, 1996).…”

Section: Introductionmentioning

confidence: 98%

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Critical view on the monochlorodimedone assay utilized to detect haloperoxidase activity

Wagner¹,

Molitor²,

König³

2008

Phytochemistry

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Recombinant flavin‐dependent halogenases are functional in tobacco chloroplasts without co‐expression of flavin reductase genes

Fräbel

Krischke

Staniek

et al. 2016

Biotechnology Journal

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Halogenation of natural compounds in planta is rare. Herein, a successful engineering of tryptophan 6-halogenation into the plant context by heterologous expression of the Streptomyces toxytricini Stth gene and localization of its enzymatic product in various tobacco cell compartments is described. When co-expressed with the flavin reductase rebF from Lechevalieria aerocolonigenes, Stth efficiently produced chlorinated tryptophan in the cytosol. Further, supplementation of KBr yielded the brominated metabolite. More strikingly, targeting of the protein to the chloroplasts enabled effective halogenation of tryptophan even in absence of the partner reductase, providing crucial evidence for sufficient, organelle-specific supply of the FADH cofactor to drive halogen integration. Incorporation of an alternative enzyme, the 7-halogenase RebH from L. aerocolonigenes, into the metabolic set-up resulted in the formation of 6,7-dichlorotryptophan. Finally, expression of tryptophan decarboxylase (tdc) in concert with stth led to the generation of 6-chlorotryptamine, a new-to-nature precursor of monoterpenoid indole alkaloids. In sum, the report highlights the tremendous application potential of plants as a unique chassis for the engineering of rare and valuable halogenated natural products, with chloroplasts as the cache of reduction equivalents driving metabolic reactions.

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Enzymatic Incorporation of Halogen Atoms into Natural Compounds

Cited by 15 publications

References 56 publications

Flavin‐dependent Tryptophan Halogenases and Their Use in Formation of Novel Tryptophan Derived Compounds

Flavin‐dependent Tryptophan Halogenases and Their Use in Formation of Novel Tryptophan Derived Compounds

Critical view on the monochlorodimedone assay utilized to detect haloperoxidase activity

Recombinant flavin‐dependent halogenases are functional in tobacco chloroplasts without co‐expression of flavin reductase genes

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