1.21.98.2: dichlorochromopyrrolate synthase
This is an abbreviated version!
For detailed information about dichlorochromopyrrolate synthase, go to the full flat file.
Reaction
2 3-(7-chloroindol-3-yl)-2-iminopropanoate + = + + 2 H2O
Synonyms
EC 1.21.3.9, EC 4.3.1.26, RebD
ECTree
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Substrates Products
Substrates Products on EC 1.21.98.2 - dichlorochromopyrrolate synthase
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REACTION DIAGRAM
(2E)-2-[(E)-[1-carboxy-2-(1H-indol-3-yl)ethylidene]amino]-3-(2,3-dihydro-1H-indol-3-yl)prop-2-enoic acid + O2
3-(2,3-dihydro-1H-indol-3-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylic acid + NH3 + H2O
(2E)-2-[(E)-[1-carboxy-2-(7-chloro-1H-indol-3-yl)ethylidene]amino]-3-(7-chloro-2,3-dihydro-1H-indol-3-yl)prop-2-enoic acid + O2
3-(7-chloro-2,3-dihydro-1H-indol-3-yl)-4-(7-chloro-1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylic acid + NH3 + H2O
7-chloroindole-3-pyruvic acid + 7-chlorotryptophan + O2
11,11'-dichlorochromopyrrolic acid + NH3 + H2O
(2E)-2-[(E)-[1-carboxy-2-(1H-indol-3-yl)ethylidene]amino]-3-(2,3-dihydro-1H-indol-3-yl)prop-2-enoic acid + O2
3-(2,3-dihydro-1H-indol-3-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylic acid + NH3 + H2O
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(2E)-2-[(E)-[1-carboxy-2-(1H-indol-3-yl)ethylidene]amino]-3-(2,3-dihydro-1H-indol-3-yl)prop-2-enoic acid + O2
3-(2,3-dihydro-1H-indol-3-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylic acid + NH3 + H2O
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(2E)-2-[(E)-[1-carboxy-2-(7-chloro-1H-indol-3-yl)ethylidene]amino]-3-(7-chloro-2,3-dihydro-1H-indol-3-yl)prop-2-enoic acid + O2
3-(7-chloro-2,3-dihydro-1H-indol-3-yl)-4-(7-chloro-1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylic acid + NH3 + H2O
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(2E)-2-[(E)-[1-carboxy-2-(7-chloro-1H-indol-3-yl)ethylidene]amino]-3-(7-chloro-2,3-dihydro-1H-indol-3-yl)prop-2-enoic acid + O2
3-(7-chloro-2,3-dihydro-1H-indol-3-yl)-4-(7-chloro-1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylic acid + NH3 + H2O
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dichlorochromopyrrolate + NH3 + 2 H2O
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2 3-(7-chloroindol-3-yl)-2-iminopropanoate + H2O2
dichlorochromopyrrolate + NH3 + 2 H2O
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the enzyme performs an unusual biosynthetic step for a hemoprotein in that it forms C-C bonds that link the Trp-derived moieties together
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dichlorochromopyrrolate + NH3 + H2O
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2-imino-3-(7-chloroindol-3-yl)propanoate + O2
dichlorochromopyrrolate + NH3 + H2O
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2 dichlorochromopyrrolate + 2 NH3 + 2 H2O
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4 2-imino-3-(7-chloroindol-3-yl)propanoate + O2
2 dichlorochromopyrrolate + 2 NH3 + 2 H2O
rebeccamycin biosynthetic pathway
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4 2-imino-3-(7-chloroindol-3-yl)propanoate + O2
2 dichlorochromopyrrolate + 2 NH3 + 2 H2O
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4 2-imino-3-(7-chloroindol-3-yl)propanoate + O2
2 dichlorochromopyrrolate + 2 NH3 + 2 H2O
rebeccamycin biosynthetic pathway
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4 2-imino-3-(7-chloroindol-3-yl)propanoate + O2
2 dichlorochromopyrrolate + 2 NH3 + 2 H2O
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4 2-imino-3-(7-chloroindol-3-yl)propanoate + O2
2 dichlorochromopyrrolate + 2 NH3 + 2 H2O
rebeccamycin biosynthetic pathway
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11,11'-dichlorochromopyrrolic acid + NH3 + H2O
RebD is involved in the construction of a bisindole structure by catalyzing a coupling reaction between 7-chlorotryptophan and 7-chloroindole-3-pyruvic acid
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7-chloroindole-3-pyruvic acid + 7-chlorotryptophan + O2
11,11'-dichlorochromopyrrolic acid + NH3 + H2O
RebD is involved in the construction of a bisindole structure by catalyzing a coupling reaction between 7-chlorotryptophan and 7-chloroindole-3-pyruvic acid
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RebD acts as an efficient catalase, effecting the disproportionation of hydrogen peroxide to give oxygen and water
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additional information
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the enzyme has both catalase and chromopyrrolic acid synthase activity. The enzyme acts as an efficient catalase, effecting the disproportionation of hydrogen peroxide to give oxygen and (presumably) water. The enzyme on its own is incompetent with L-tryptophan
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additional information
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RebD acts as an efficient catalase, effecting the disproportionation of hydrogen peroxide to give oxygen and water
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additional information
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the enzyme has both catalase and chromopyrrolic acid synthase activity. The enzyme acts as an efficient catalase, effecting the disproportionation of hydrogen peroxide to give oxygen and (presumably) water. The enzyme on its own is incompetent with L-tryptophan
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additional information
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RebD is a heme-containing peroxidase-like enzyme that catalyzes the oxidative linking of two tryptophan skeletons to form dichlorochromopyrrolic acid. RebD reacts as a peroxidase forming two indole-3-pyruvic acid imine radicals that recombine as a CĀC bond in the chromopyrrolic acid. When catalase is included to remove H2O2, chromopyrrolic acid can still be formed because the indole-3-pyruvic acid imine rapidly reduces RebD, which reacts with O2, utilizing oxidase-peroxidase chemistry to produce chromopyrrolic acid. Reduced RebD can also react with H2O2 forming Cpd II (state of a hemoprotein that is 1 equivalent of oxidation greater than the ferric form and contains an oxoferryl center) directly, which can oxidize indole-3-pyruvic acid imine. Competitng robust catalase activity of RebD
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additional information
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the enzyme is reduced by indole-3-pyruvic acid imine
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