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Literature summary for 1.14.19.9 extracted from

  • Heemstra, J.R.Jr.; Walsh, C.T.
    Tandem action of the O2- and FADH2-dependent halogenases KtzQ and KtzR produce 6,7-dichlorotryptophan for Kutzneride assembly (2008), J. Am. Chem. Soc., 130, 14024-14025 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 1.14.19.9

Cloned(Commentary)

Cloned (Comment) Organism
gene ktzQ, cloned from genomic DNA, DNA and amino acid sequence determination and analysis, recombinant expression as soluble N-terminally His6-tagged enzyme in Escherichia coli strain BL21(DE3) Kutzneria sp. 744

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.002
-
 L-tryptophan about, pH 7.0, temperature not specified in the publication, recombinant His-tagged enzyme Kutzneria sp. 744
0.002
-
 6-chloro-L-tryptophan about, pH 7.0, temperature not specified in the publication, recombinant His-tagged enzyme Kutzneria sp. 744

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
L-tryptophan + FADH2 + chloride + O2 + H+ Kutzneria sp. 744
-
 7-chloro-L-tryptophan + FAD + 2 H2O
-
 ?

Organism

Organism UniProt Comment Textmining
Kutzneria sp. 744 A8CF75
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant soluble N-terminally His6-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chrmatography and gel filtration Kutzneria sp. 744

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
6-chloro-L-tryptophan + FADH2 + chloride + O2 + H+
-
 Kutzneria sp. 744 6,7-dichloro-L-tryptophan + FAD + 2 H2O
-
 ?
L-tryptophan + FADH2 + chloride + O2 + H+
-
 Kutzneria sp. 744 7-chloro-L-tryptophan + FAD + 2 H2O
-
 ?
additional information KtzQ shows no activity for chlorination of piperazic acid or gamma,delta-dehydropiperazic acid but is active when incubated with L-Trp. Substrate specificity of KtzQ in a coupled assay system with flavin reductase KtzS, overview. Product analysis with NMR spectroscopy and ESI-mass spectrometry. KtzQ is a regiospecific tryptophan-7-halogenase Kutzneria sp. 744 ?
-
 ?

Synonyms

Synonyms Comment Organism
KtzQ
-
 Kutzneria sp. 744
PrnA
-
 Kutzneria sp. 744

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.0012
-
 6-chloro-L-tryptophan pH 7.0, temperature not specified in the publication, recombinant His-tagged enzyme Kutzneria sp. 744
0.0032
-
 L-tryptophan pH 7.0, temperature not specified in the publication, recombinant His-tagged enzyme Kutzneria sp. 744

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7
-
 assay at Kutzneria sp. 744

Cofactor

Cofactor Comment Organism Structure
FAD
-
 Kutzneria sp. 744

General Information

General Information Comment Organism
metabolism tryptophan 7-halogenase catalyzes chlorination of free tryptophan to 7-chlorotryptophan, which is the first step in the antibiotic pyrrolnitrin biosynthesis. Purified KtzQ and KtzR are tandem acting halogenases that catalyze the regiospecific dichlorination of L-tryptophan to produce 6,7-dichloro-L-tryptophan, KtzQ is specific for L-Trp or 6-chloro-L-Trp halogenation at C-7, while KtzR is specific for halogenation of C-6 of 7-chloro-L-Trp Kutzneria sp. 744
physiological function enzyme KtzQ (along with the flavin reductase KtzS) acts to chlorinate at the 7-position of L-tryptophan Kutzneria sp. 744