Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
twitter

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:
flavin-dependent monooxygenase RebC Inferred from experiment : rebC ( Lechevalieria aerocolonigenes )
P450 oxygenase RebP Inferred from experiment : rebP ( Lechevalieria aerocolonigenes )

In Pathway: rebeccamycin biosynthesis

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

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: ?

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 18.5 on Mon Nov 24, 2014, BIOCYC13A.