KEGG   ENZYME: 1.21.98.2
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
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)
R09566
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
ec01110  Biosynthesis of secondary metabolites
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

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