|Superclasses:||Reactions Classified By Conversion Type → Simple Reactions → Chemical Reactions|
|Reactions Classified By Substrate → Small-Molecule Reactions|
EC Number: 220.127.116.11
Enzymes and Genes:
|Lechevalieria aerocolonigenes:||P450 oxygenase RebP: rebP|
flavin-dependent monooxygenase RebC: 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): -421.74683 [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
©2016 SRI International, 333 Ravenswood Avenue, Menlo Park, CA 94025-3493