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MetaCyc Reaction: 1.13.12.17

Superclasses: Reactions Classified By Conversion Type Simple Reactions Chemical Reactions
Reactions Classified By Substrate Small-Molecule Reactions

EC Number: 1.13.12.17

Enzymes and Genes:

Lechevalieria aerocolonigenes : P450 oxygenase RebP Inferred from experiment : rebP
flavin-dependent monooxygenase RebC Inferred from experiment : 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 Inferred 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:1.13.12.17 , ENZYME:EC:1.13.12.17 , IUBMB-ExplorEnz:EC:1.13.12.17

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


References

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 SRI International Pathway Tools version 19.0 on Fri Jul 31, 2015, BIOCYC13B.