MetaCyc Reaction:

Superclasses: Reactions Classified By Conversion TypeSimple ReactionsChemical Reactions
Reactions Classified By SubstrateSmall-Molecule Reactions

EC Number:

Enzymes and Genes:

Lechevalieria aerocolonigenes: P450 oxygenase RebPInferred from experiment: rebP
flavin-dependent monooxygenase RebCInferred from experiment: rebC

In Pathway: rebeccamycin biosynthesis

The direction shown, i.e. which substrates are on the left and right sides, 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. 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): -421.74683Inferred by computational analysis [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].

Gene-Reaction Schematic

Gene-Reaction Schematic

Unification Links: KEGG:R09567, Rhea:27314

Relationship Links: BRENDA:EC:, ENZYME:EC:, IUBMB-ExplorEnz:EC:

Created 31-Aug-2009 by Caspi R, SRI International


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

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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

Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Mon Nov 30, 2015, biocyc14.