KEGG   ENZYME: 1.13.12.17Help
Entry
EC 1.13.12.17               Enzyme                                 

Name
dichloroarcyriaflavin A synthase
Class
Oxidoreductases;
Acting on single donors with incorporation of molecular oxygen (oxygenases);
With incorporation of one atom of oxygen (internal monooxygenases or internal mixed-function oxidases)
BRITE hierarchy
Sysname
dichlorochromopyrrolate,NADH:oxygen 2,5-oxidoreductase (dichloroarcyriaflavin A-forming)
Reaction(IUBMB)
dichlorochromopyrrolate + 4 O2 + 4 NADH + 4 H+ = dichloroarcyriaflavin A + 2 CO2 + 6 H2O + 4 NAD+ [RN:R09567]
Reaction(KEGG)
Substrate
dichlorochromopyrrolate [CPD:C19698];
O2 [CPD:C00007];
NADH [CPD:C00004];
H+ [CPD:C00080]
Product
dichloroarcyriaflavin A [CPD:C19699];
CO2 [CPD:C00011];
H2O [CPD:C00001];
NAD+ [CPD:C00003]
Comment
The conversion of dichlorochromopyrrolate to dichloroarcyriaflavin A is a complex process that involves two enzyme components. RebP is an NAD-dependent cytochrome P-450 oxygenase that performs an aryl-aryl bond formation yielding the six-ring indolocarbazole scaffold [1]. Along with RebC, a flavin-dependent hydroxylase, it also catalyses the oxidative decarboxylation of both carboxyl groups. The presence of RebC ensures that the only product is the rebeccamycin aglycone dichloroarcyriaflavin A [2]. The enzymes are similar, but not identical, to StaP and StaC, which are involved in the synthesis of staurosporine [3].
History
EC 1.13.12.17 created 2010
Pathway
ec00404  Staurosporine biosynthesis
ec01130  Biosynthesis of antibiotics
Orthology
K19886  flavin-dependent monooxygenase RebC
K19887  cytochrome P450 RebP
Reference
1  [PMID:17606921]
  Authors
Makino M, Sugimoto H, Shiro Y, Asamizu S, Onaka H, Nagano S
  Title
Crystal structures and catalytic mechanism of cytochrome P450 StaP that produces  the indolocarbazole skeleton.
  Journal
Proc Natl Acad Sci U S A 104:11591-6 (2007)
DOI:10.1073/pnas.0702946104
Reference
2  [PMID:16967980]
  Authors
Howard-Jones AR, Walsh CT
  Title
Staurosporine and rebeccamycin aglycones are assembled by the oxidative action of StaP, StaC, and RebC on chromopyrrolic acid.
  Journal
J Am Chem Soc 128:12289-98 (2006)
DOI:10.1021/ja063898m
Reference
3  [PMID:15625109]
  Authors
Sanchez C, Zhu L, Brana AF, Salas AP, Rohr J, Mendez C, Salas JA
  Title
Combinatorial biosynthesis of antitumor indolocarbazole compounds.
  Journal
Proc Natl Acad Sci U S A 102:461-6 (2005)
DOI:10.1073/pnas.0407809102
Other DBs
ExplorEnz - The Enzyme Database: 1.13.12.17
IUBMB Enzyme Nomenclature: 1.13.12.17
ExPASy - ENZYME nomenclature database: 1.13.12.17
BRENDA, the Enzyme Database: 1.13.12.17

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