|Superclasses:||Reactions Classified By Conversion Type → Simple Reactions → Chemical Reactions|
|Reactions Classified By Substrate → Small-Molecule Reactions|
EC Number: 184.108.40.206
Enzymes and Genes:
|Lechevalieria aerocolonigenes :||P450 oxygenase RebP
flavin-dependent monooxygenase RebC : rebC
In Pathway: rebeccamycin biosynthesis
The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.
Most BioCyc compounds have been protonated to a reference pH value of 7.3, and some reactions have been computationally balanced for hydrogen by adding free protons. Please see the PGDB Concepts Guide for more information.
Mass balance status: Balanced.
Enzyme Commission Primary Name: dichloroarcyriaflavin A synthase
Standard Gibbs Free Energy (ΔrG'° in kcal/mol): -421.74683 [Latendresse13]
Enzyme Commission Summary:
The conversion of dichlorochromopyrrolate to dichloroarcyriaflavin A is a complex process that involves two enzyme components. RebP is an NAD-dependent cytochrome P450 oxygenase that performs an aryl-aryl bond formation yielding the six-ring indolocarbazole scaffold [Makino07]. 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 [HowardJones06]. The enzymes are similar, but not identical, to StaP and StaC, which are involved in the synthesis of staurosporine [Sanchez05a].
HowardJones06: Howard-Jones AR, Walsh CT (2006). "Staurosporine and rebeccamycin aglycones are assembled by the oxidative action of StaP, StaC, and RebC on chromopyrrolic acid." J Am Chem Soc 128(37);12289-98. PMID: 16967980
Makino07: Makino M, Sugimoto H, Shiro Y, Asamizu S, Onaka H, Nagano S (2007). "Crystal structures and catalytic mechanism of cytochrome P450 StaP that produces the indolocarbazole skeleton." Proc Natl Acad Sci U S A 104(28);11591-6. PMID: 17606921
Sanchez05a: Sanchez C, Zhu L, Brana AF, Salas AP, Rohr J, Mendez C, Salas JA (2005). "Combinatorial biosynthesis of antitumor indolocarbazole compounds." Proc Natl Acad Sci U S A 102(2);461-6. PMID: 15625109
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