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
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Natural Substrates Products on EC 1.21.98.2 - dichlorochromopyrrolate synthase
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REACTION DIAGRAM
2 3-(7-chloroindol-3-yl)-2-iminopropanoate + H2O2
dichlorochromopyrrolate + NH3 + 2 H2O
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7-chloroindole-3-pyruvic acid + 7-chlorotryptophan + O2
11,11'-dichlorochromopyrrolic acid + NH3 + H2O
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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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
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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