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IUBMB Comments Contains a noncovalently bound FAD [1,2]. This enzyme catalyses a step in the biosynthesis of rebeccamycin, an indolocarbazole alkaloid produced by the bacterium Lechevalieria aerocolonigenes . During catalysis, the bound FAD is reoxidized at the expense of molecular oxygen, producing one molecule of hydrogen peroxide. The enzyme shows significant preference for 7-chloro-L -tryptophan over L -tryptophan .
Synonyms RebO ,
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RebO
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7-chloro-L-tryptophan + O2 = 2-imino-3-(7-chloroindol-3-yl)propanoate + H2O2
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MetaCyc
K-252 biosynthesis, rebeccamycin biosynthesis, staurosporine biosynthesis, violacein biosynthesis
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7-chloro-L-tryptophan:oxygen oxidoreductase
Contains a noncovalently bound FAD [1,2]. This enzyme catalyses a step in the biosynthesis of rebeccamycin, an indolocarbazole alkaloid produced by the bacterium Lechevalieria aerocolonigenes. During catalysis, the bound FAD is reoxidized at the expense of molecular oxygen, producing one molecule of hydrogen peroxide. The enzyme shows significant preference for 7-chloro-L-tryptophan over L-tryptophan [1].
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1-methyl-L-tryptophan + O2
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Substrates: -
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5-fluoro-L-tryptophan + O2
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Substrates: -
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5-methyl-DL-tryptophan + O2
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Substrates: -
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7-chloro-L-tryptophan + O2
2-imino-3-(7-chloroindol-3-yl)propanoate + H2O2
L-Trp + O2
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Substrates: -
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L-tryptophan + O2
2-imino-3-(indol-3-yl)propanoate + H2O2
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Substrates: -
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additional information
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Substrates: L-tryptophanamide and N-acetyl-tryptophan are not accepted as substrates by RebO
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7-chloro-L-tryptophan + O2
2-imino-3-(7-chloroindol-3-yl)propanoate + H2O2
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Substrates: -
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7-chloro-L-tryptophan + O2
2-imino-3-(7-chloroindol-3-yl)propanoate + H2O2
Substrates: -
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7-chloro-L-tryptophan + O2
2-imino-3-(7-chloroindol-3-yl)propanoate + H2O2
Substrates: rebeccamycin biosynthetic pathway
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7-chloro-L-tryptophan + O2
2-imino-3-(7-chloroindol-3-yl)propanoate + H2O2
Substrates: RebO is specific for the L-Trp enantiomer. 7-chloro-L-Trp is the preferred substrate
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7-chloro-L-tryptophan + O2
2-imino-3-(7-chloroindol-3-yl)propanoate + H2O2
L-tryptophan + O2
2-imino-3-(indol-3-yl)propanoate + H2O2
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Substrates: -
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7-chloro-L-tryptophan + O2
2-imino-3-(7-chloroindol-3-yl)propanoate + H2O2
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Substrates: -
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7-chloro-L-tryptophan + O2
2-imino-3-(7-chloroindol-3-yl)propanoate + H2O2
Substrates: rebeccamycin biosynthetic pathway
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FAD
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FAD
contains noncovalently bound flavin of 0.58 mol per mol of protein. RebO protein that is overexpressed without supplementation of FAD in Escherichia coli BL21(DE3) contains less than 0.5 mol of noncovalently bound flavin per mol of enzyme
FAD
noncovalently bound, FAD occupancy at 70%
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1.43
1-methyl-L-tryptophan
pH 7.8, 30°C
1.84
5-fluoro-L-tryptophan
pH 7.8, 30°C
0.088
7-chloro-L-tryptophan
pH 7.8, 30°C
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0.0255
1-methyl-L-tryptophan
pH 7.8, 30°C
0.239
5-fluoro-L-tryptophan
pH 7.8, 30°C
0.664
7-chloro-L-tryptophan
pH 7.8, 30°C
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0.0178
1-methyl-L-tryptophan
pH 7.8, 30°C
0.13
5-fluoro-L-tryptophan
pH 7.8, 30°C
7.55
7-chloro-L-tryptophan
pH 7.8, 30°C
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UniProt
brenda
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brenda
ATCC 39243
UniProt
brenda
Highest Expressing Human Cell Lines
Filter by:
Cell Line Links
Gene Links
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53412
2 * 53412, calculated from sequence
56000
x * 56000, SDS-PAGE
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dimer
2 * 53412, calculated from sequence
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x * 56000, SDS-PAGE
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Ni-NTA agarose column chromatography
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expressed in Escherichia coli C41 cells
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expression in Escherichia coli
expression of N-His6-tagged RebO in Escherichia coli
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Howard-Jones, A.R.; Walsh, C.T.
Enzymatic generation of the chromopyrrolic acid scaffold of rebeccamycin by the tandem action of RebO and RebD
Biochemistry
44
15652-15663
2005
Lentzea aerocolonigenes (Q8KHS0)
brenda
Nishizawa, T.; Aldrich, C.C.; Sherman, D.H.
Molecular analysis of the rebeccamycin L-amino acid oxidase from Lechevalieria aerocolonigenes ATCC 39243
J. Bacteriol.
187
2084-2092
2005
Lentzea aerocolonigenes (Q8KHS0)
brenda
Spolitak, T.; Ballou, D.P.
Evidence for catalytic intermediates involved in generating the chromopyrrolic acid scaffold of rebeccamycin by RebO and RebD
Arch. Biochem. Biophys.
573
111-119
2015
Lentzea aerocolonigenes
brenda
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