PMID:15743957

Nishizawa T, Aldrich CC, Sherman DH

Molecular analysis of the rebeccamycin L-amino acid oxidase from Lechevalieria aerocolonigenes ATCC 39243.

J Bacteriol 187:2084-92 (2005)
DOI:10.1128/JB.187.6.2084-2092.2005

[ag:BAC10676]

PMID:21290541

Groom K, Bhattacharya A, Zechel DL

Rebeccamycin and staurosporine biosynthesis: insight into the mechanisms of the flavin-dependent monooxygenases RebC and StaC.

Chembiochem 12:396-400 (2011)
DOI:10.1002/cbic.201000580

PMID:15743957

Nishizawa T, Aldrich CC, Sherman DH

Molecular analysis of the rebeccamycin L-amino acid oxidase from Lechevalieria aerocolonigenes ATCC 39243.

J Bacteriol 187:2084-92 (2005)
DOI:10.1128/JB.187.6.2084-2092.2005

[ag:BAC10677]

PMID:17705392

Howard-Jones AR, Walsh CT

Nonenzymatic oxidative steps accompanying action of the cytochrome P450 enzymes StaP and RebP in the biosynthesis of staurosporine and rebeccamycin.

J Am Chem Soc 129:11016-7 (2007)
DOI:10.1021/ja0743801

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

dichlorochromopyrrolate,NADH:oxygen 2,5-oxidoreductase (dichloroarcyriaflavin A-forming)

dichlorochromopyrrolate + 4 O2 + 4 NADH + 4 H+ = dichloroarcyriaflavin A + 2 CO2 + 6 H2O + 4 NAD+ [RN:R09567]

R09567
Reaction

dichlorochromopyrrolate [CPD:C19698];
O2 [CPD:C00007];
NADH [CPD:C00004];
H+ [CPD:C00080]

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].

EC 1.13.12.17 created 2010

1  [PMID:17606921]

Makino M, Sugimoto H, Shiro Y, Asamizu S, Onaka H, Nagano S

Crystal structures and catalytic mechanism of cytochrome P450 StaP that produces  the indolocarbazole skeleton.

Proc Natl Acad Sci U S A 104:11591-6 (2007)
DOI:10.1073/pnas.0702946104

2  [PMID:16967980]

Howard-Jones AR, Walsh CT

Staurosporine and rebeccamycin aglycones are assembled by the oxidative action of StaP, StaC, and RebC on chromopyrrolic acid.

J Am Chem Soc 128:12289-98 (2006)
DOI:10.1021/ja063898m

3  [PMID:15625109]

Sanchez C, Zhu L, Brana AF, Salas AP, Rohr J, Mendez C, Salas JA

Combinatorial biosynthesis of antitumor indolocarbazole compounds.

Proc Natl Acad Sci U S A 102:461-6 (2005)
DOI:10.1073/pnas.0407809102