KEGG   ORTHOLOGY: K19885Help
Entry
K19885                      KO                                     

Name
rebD
Definition
dichlorochromopyrrolate synthase / catalase [EC:1.21.98.2 1.11.1.6]
Pathway
ko00404  Staurosporine biosynthesis
ko01100  Metabolic pathways
ko01130  Biosynthesis of antibiotics
Module
M00789  Rebeccamycin biosynthesis, tryptophan => rebeccamycin
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00404 Staurosporine biosynthesis
    K19885  rebD; dichlorochromopyrrolate synthase / catalase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.11  Acting on a peroxide as acceptor
   1.11.1  Peroxidases
    1.11.1.6  catalase
     K19885  rebD; dichlorochromopyrrolate synthase / catalase
  1.21  Catalysing the reaction X-H + Y-H = X-Y
   1.21.98  With other, known, physiological acceptors
    1.21.98.2  dichlorochromopyrrolate synthase
     K19885  rebD; dichlorochromopyrrolate synthase / catalase
BRITE hierarchy
Other DBs
RN: R09566
GO: 0004096
Genes
AG: BAC10675(rebD)
TaxonomyKoalaUniProt
Reference
  Authors
Nishizawa T, Aldrich CC, Sherman DH
  Title
Molecular analysis of the rebeccamycin L-amino acid oxidase from Lechevalieria aerocolonigenes ATCC 39243.
  Journal
J Bacteriol 187:2084-92 (2005)
DOI:10.1128/JB.187.6.2084-2092.2005
  Sequence
Reference
  Authors
Howard-Jones AR, Walsh CT
  Title
Enzymatic generation of the chromopyrrolic acid scaffold of rebeccamycin by the tandem action of RebO and RebD.
  Journal
Biochemistry 44:15652-63 (2005)
DOI:10.1021/bi051706e

KEGG   ENZYME: 1.21.98.2Help
Entry
EC 1.21.98.2                Enzyme                                 

Name
dichlorochromopyrrolate synthase;
RebD;
chromopyrrolic acid synthase;
chromopyrrolate synthase
Class
Oxidoreductases;
Catalysing the reaction X-H + Y-H = X-Y;
With other, known, physiological acceptors
BRITE hierarchy
Sysname
3-(7-chloroindol-3-yl)-2-iminopropanoate ammonia-lyase (dichlorochromopyrrolate-forming)
Reaction(IUBMB)
2 3-(7-chloroindol-3-yl)-2-iminopropanoate + H2O2 = dichlorochromopyrrolate + NH3 + 2 H2O [RN:R09566]
Reaction(KEGG)
Substrate
3-(7-chloroindol-3-yl)-2-iminopropanoate;
H2O2 [CPD:C00027]
Product
dichlorochromopyrrolate [CPD:C19698];
NH3 [CPD:C00014];
H2O [CPD:C00001]
Comment
This enzyme catalyses a step in the biosynthesis of rebeccamycin, an indolocarbazole alkaloid produced by the bacterium Lechevalieria aerocolonigenes. The enzyme is a dimeric heme-protein oxidase that catalyses the oxidative dimerization of two L-tryptophan-derived molecules to form dichlorochromopyrrolic acid, the precursor for the fused six-ring indolocarbazole scaffold of rebeccamycin [1]. Contains one molecule of heme b per monomer, as well as non-heme iron that is not part of an iron-sulfur center [2]. In vivo the enzyme uses hydrogen peroxide, formed by the enzyme upstream in the biosynthetic pathway (EC 1.4.3.23, 7-chloro-L-tryptophan oxidase) as the electron acceptor. However, the enzyme is also able to catalyse the reaction using molecular oxygen [3].
History
EC 1.21.98.2 created 2010 as EC 4.3.1.26, transferred 2013 to EC 1.21.3.9, transferred 2016 to EC 1.21.98.2
Pathway
ec00404  Staurosporine biosynthesis
ec01100  Metabolic pathways
ec01130  Biosynthesis of antibiotics
Orthology
K19885  dichlorochromopyrrolate synthase / catalase
Reference
1  [PMID:16417354]
  Authors
Nishizawa T, Gruschow S, Jayamaha DH, Nishizawa-Harada C, Sherman DH
  Title
Enzymatic assembly of the bis-indole core of rebeccamycin.
  Journal
J Am Chem Soc 128:724-5 (2006)
DOI:10.1021/ja056749x
Reference
2  [PMID:16313168]
  Authors
Howard-Jones AR, Walsh CT
  Title
Enzymatic generation of the chromopyrrolic acid scaffold of rebeccamycin by the tandem action of RebO and RebD.
  Journal
Biochemistry 44:15652-63 (2005)
DOI:10.1021/bi051706e
  Sequence
Reference
3  [PMID:25837855]
  Authors
Spolitak T, Ballou DP
  Title
Evidence for catalytic intermediates involved in generating the chromopyrrolic acid scaffold of rebeccamycin by RebO and RebD.
  Journal
Arch Biochem Biophys 573:111-9 (2015)
DOI:10.1016/j.abb.2015.03.020
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.21.98.2
IUBMB Enzyme Nomenclature: 1.21.98.2
ExPASy - ENZYME nomenclature database: 1.21.98.2
BRENDA, the Enzyme Database: 1.21.98.2

KEGG   REACTION: R09566Help
Entry
R09566                      Reaction                               

Name
2-imino-3-(7-chloroindol-3-yl)propanoate ammonia-lyase (dichlorochromopyrrolate-forming);
2-imino-3-(7-chloroindol-3-yl)propanoate:oxygen oxidoreductase (dichlorochromopyrrolate-forming)
Definition
4 2-Imino-3-(7-chloroindol-3-yl)propanoate + Oxygen <=> 2 3,4-Bis(7-chloroindol-3-yl)pyrrole-2,5-dicarboxylate + 2 Ammonia + 2 H2O
Equation
4 C19688 + C00007 <=> 2 C19698 + 2 C00014 + 2 C00001
Reaction class
RC02568  C19688_C19698
Enzyme
Pathway
rn00404  Staurosporine biosynthesis
rn01100  Metabolic pathways
rn01130  Biosynthesis of antibiotics
Module
M00789  Rebeccamycin biosynthesis, tryptophan => rebeccamycin
Orthology
K19885  dichlorochromopyrrolate synthase / catalase [EC:1.21.98.2 1.11.1.6]
Other DBs
RHEA: 27396

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