1.14.19.9: tryptophan 7-halogenase
This is an abbreviated version!
For detailed information about tryptophan 7-halogenase, go to the full flat file.
Word Map on EC 1.14.19.9
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1.14.19.9
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fadh2-dependent
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dichlorination
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halometabolites
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rebeccamycin
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alpha-ketoglutarate-dependent
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haloperoxidases
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syringomycin
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alphakg-dependent
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pyrrolnitrin
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alphakg
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l-thr
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organohalogens
- 1.14.19.9
-
fadh2-dependent
-
dichlorination
-
halometabolites
- rebeccamycin
-
alpha-ketoglutarate-dependent
- haloperoxidases
-
syringomycin
-
alphakg-dependent
- pyrrolnitrin
-
alphakg
- l-thr
-
organohalogens
Reaction
Synonyms
EC 1.14.14.7, FAD-dependent halogenase, flavin-dependent halogenase, flavin-dependent tryptophan halogenase, halogenase, KtzQ, L-tryptophan-7-halogenase, PrnA, RebH, Trp 7-hal, Trp halogenase, Trp-7-Hal, Trp-7-halogenase
ECTree
1.14.19.9 tryptophan 7-halogenaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 1.14.19.9 - tryptophan 7-halogenase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
5-amino-L-tryptophan + FADH2 + chloride + O2 + H+
7-chloro-5-amino-L-tryptophan + FAD + 2 H2O
-
-
-
?
5-bromo-L-tryptophan + FADH2 + chloride + O2 + H+
7-chloro-5-bromo-L-tryptophan + FAD + 2 H2O
-
-
-
?
5-fluoro-L-tryptophan + FADH2 + chloride + O2 + H+
7-chloro-5-fluoro-L-tryptophan + FAD + 2 H2O
-
-
-
?
5-hydroxy-L-tryptophan + FADH2 + chloride + O2 + H+
7-chloro-5-hydroxy-L-tryptophan + FAD + 2 H2O
5-methyl-L-tryptophan + FADH2 + chloride + O2 + H+
7-chloro-5-methyl-L-tryptophan + FAD + 2 H2O
-
-
-
?
6-chloro-L-tryptophan + FADH2 + chloride + O2 + H+
6,7-dichloro-L-tryptophan + FAD + 2 H2O
D-tryptophan + FADH2 + bromide + O2 + H+
7-bromo-D-tryptophan + FAD + 2 H2O
regioselective halogenation, recombinant enzyme
-
-
?
L-tryptophan + FADH2 + bromide + O2 + H+
7-bromo-L-tryptophan + FAD + 2 H2O
best substrates, regioselective halogenation, recombinant enzyme
-
-
?
tryptamine + FADH2 + Cl- + O2 + H+
7-chloro-L-tryptamine + FAD + H2O
-
-
-
?
tryptophan + FADH2 + chloride + O2 + H+
7-chloro-L-tryptophan + FAD + 2 H2O
-
-
-
?
tryptophan + FADH2 + Cl- + O2 + H+
7-chloro-L-tryptophan + FAD + 2 H2O
-
-
-
-
?
tryptophan + FADH2 + Cl- + O2 + H+
7-chloro-L-tryptophan + FAD + H2O
-
-
-
?
tryptophan + FADH2 + O2 + Cl- + H+
7-chlorotryptophan + FAD + H2O
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initial step of rebeccamycin biosynthesis
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-
?
5-hydroxy-L-tryptophan + FADH2 + chloride + O2 + H+
7-chloro-5-hydroxy-L-tryptophan + FAD + 2 H2O
-
-
-
?
5-hydroxy-L-tryptophan + FADH2 + chloride + O2 + H+
7-chloro-5-hydroxy-L-tryptophan + FAD + 2 H2O
regioselective halogenation, recombinant enzyme
-
-
?
6-chloro-L-tryptophan + FADH2 + chloride + O2 + H+
6,7-dichloro-L-tryptophan + FAD + 2 H2O
-
-
-
?
6-chloro-L-tryptophan + FADH2 + chloride + O2 + H+
6,7-dichloro-L-tryptophan + FAD + 2 H2O
-
-
-
?
L-tryptophan + FADH2 + Br- + O2 + H+
7-bromo-L-tryptophan + FAD + H2O
-
-
-
?
L-tryptophan + FADH2 + Br- + O2 + H+
7-bromo-L-tryptophan + FAD + H2O
-
identity of product is confirmed by ESI-MS and 1H-NMR. Reaction is selective for the 7-position. Brominating activity is about 75% of chlorinating activity
-
?
L-tryptophan + FADH2 + Br- + O2 + H+
7-bromo-L-tryptophan + FAD + H2O
Lentzea aerocolonigenes 39243
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identity of product is confirmed by ESI-MS and 1H-NMR. Reaction is selective for the 7-position. Brominating activity is about 75% of chlorinating activity
-
?
L-tryptophan + FADH2 + chloride + O2 + H+
7-chloro-L-tryptophan + FAD + 2 H2O
-
-
-
?
L-tryptophan + FADH2 + chloride + O2 + H+
7-chloro-L-tryptophan + FAD + 2 H2O
-
-
-
?
L-tryptophan + FADH2 + Cl- + O2
7-chloro-L-tryptophan + FAD + H2O
-
formation of 7-chlorotryptophan as the initial step in the biosynthesis of antitumor agent rebeccamycin
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-
?
L-tryptophan + FADH2 + Cl- + O2
7-chloro-L-tryptophan + FAD + H2O
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reaction of FADH2, Cl-, and O2 in the active site, involving active site Lys79, generates the powerful oxidant HOCl, which was presumed to carry out the chlorination reaction, formation of a long-living chlorinating intermediate, which remains on the enzyme after removal of FAD and transfers chlorine to tryptophan with kinetically competent rates, substrate binding structure, overview
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-
?
L-tryptophan + FADH2 + Cl- + O2 + H+
7-chloro-L-tryptophan + FAD + H2O
-
-
-
?
L-tryptophan + FADH2 + Cl- + O2 + H+
7-chloro-L-tryptophan + FAD + H2O
-
identity of product is confirmed by ESI-MS and 1H-NMR
-
?
L-tryptophan + FADH2 + Cl- + O2 + H+
7-chloro-L-tryptophan + FAD + H2O
Lentzea aerocolonigenes 39243
-
identity of product is confirmed by ESI-MS and 1H-NMR
-
?
L-tryptophan + FADH2 + Cl- + O2 + H+
7-chloro-L-tryptophan + FAD + H2O
-
-
-
?
L-tryptophan + FADH2 + Cl- + O2 + H+
7-chloro-L-tryptophan + FAD + H2O
-
regioselective reaction
-
-
?
L-tryptophan + FADH2 + Cl- + O2 + H+
7-chloro-L-tryptophan + FAD + H2O
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the enzyme is involved in biosynthesis of pyrrolnitrin
-
-
?
L-tryptophan + FADH2 + Cl- + O2 + H+
7-chloro-L-tryptophan + FAD + H2O
the enzyme is involved in biosynthesis of pyrrolnitrin
-
-
?
tryptophan + FADH2 + Cl- + O2 + H+
7-chloro-tryptophan + FAD + H2O
-
-
-
?
tryptophan + FADH2 + Cl- + O2 + H+
7-chloro-tryptophan + FAD + H2O
rebeccamycin biosynthesis
-
-
?
tryptophan + FADH2 + Cl- + O2 + H+
7-chloro-tryptophan + FAD + H2O
-
-
-
?
tryptophan + FADH2 + Cl- + O2 + H+
7-chloro-tryptophan + FAD + H2O
-
-
-
?
tryptophan + FADH2 + Cl- + O2 + H+
7-chloro-tryptophan + FAD + H2O
chlorination of its natural substrate tryptophan exclusively at the 7-position, a position at which direct chemical chlorination is not possible
-
-
?
tryptophan + FADH2 + Cl- + O2 + H+
7-chloro-tryptophan + FAD + H2O
rebeccamycin biosynthesis
-
-
?
tryptophan + FADH2 + Cl- + O2 + H+
7-chloro-tryptophan + FAD + H2O
-
-
-
?
tryptophan + FADH2 + Cl- + O2 + H+
7-chloro-tryptophan + FAD + H2O
chlorination of its natural substrate tryptophan exclusively at the 7-position, a position at which direct chemical chlorination is not possible
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-
?
additional information
?
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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
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-
?
additional information
?
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first step in biosynthesis of rebeccamycin
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-
?
additional information
?
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O2 and presence of RebF, which catalyzes the NADH-dependent reduction of FAD to provide FADH2 for the halogenase, are required for reaction. 54% of available L-tryptophan are converted within 5 min when the reaction is prepapred anaerobically and O2 is introduced slowly. Reaction rate drops by 90% in air-saturated conditions. No substrate: fluoride, iodide
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-
?
additional information
?
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a combination of tryptophan synthase from Salmonella enterica and tryptophan-7-halogenase RebH from Lechevalieria aerocolonigenes for the regioselective halogenation of substituted tryptophan derivatives. An array of C5- and C6-substituted tryptophan derivatives is synthesized and 7-halogenated by RebH. Halogenation products of tryptophan derivatives by RebH, overview. Halogenation occurs in many cases preferably in the electronically unfavored C7 position, even in presence of deactivating ortho/para-directing groups like 5-fluoro
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-
?
additional information
?
-
Lentzea aerocolonigenes 39243
O2 and presence of RebF, which catalyzes the NADH-dependent reduction of FAD to provide FADH2 for the halogenase, are required for reaction. 54% of available L-tryptophan are converted within 5 min when the reaction is prepapred anaerobically and O2 is introduced slowly. Reaction rate drops by 90% in air-saturated conditions. No substrate: fluoride, iodide
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-
?
additional information
?
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first step in pyrrolnitrin biosynthetic pathway
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-
?
additional information
?
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Trp 7-hal can accept a number of different tryptophan, indole, and phenylpyrrole derivatives (e.g. 3-(2'-aminophenyl)pyrrole or monodechloroaminopyrrolnitrin), but only tryptophan is regioselectively chlorinated in the 7-position of the indole ring. With all the other compounds, the reaction proceeds with a relaxed regioselectivity
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-
?
additional information
?
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Trp 7-hal can accept a number of different tryptophan, indole, and phenylpyrrole derivatives (e.g. 3-(2'-aminophenyl)pyrrole or monodechloroaminopyrrolnitrin), but only tryptophan is regioselectively chlorinated in the 7-position of the indole ring. With all the other compounds, the reaction proceeds with a relaxed regioselectivity
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-
?
