KEGG   ENZYME: 1.14.13.185Help
Entry
EC 1.14.13.185              Enzyme                                 

Name
pikromycin synthase;
PikC;
CYP107L1
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
narbomycin,NADH:oxygen oxidoreductase (pikromycin-forming)
Reaction(IUBMB)
(1) narbomycin + NADPH + H+ + O2 = pikromycin + NADP+ + H2O [RN:R06464];
(2) narbomycin + NADPH + H+ + O2 = neopikromycin + NADP+ + H2O [RN:R10626];
(3) narbomycin + 2 NADPH + 2 H+ + 2 O2 = novapikromyin + 2 NADP+ + 2 H2O [RN:R10627];
(4) 10-deoxymethymycin + NADPH + H+ + O2 = methymycin + NADP+ + H2O [RN:R06463];
(5) 10-deoxymethymycin + NADPH + H+ + O2 = neomethymycin + NADP+ + H2O [RN:R06462];
(6) 10-deoxymethymycin + 2 NADPH + 2 H+ + 2 O2 = novamethymycin + 2 NADP+ + 2 H2O [RN:R10628]
Reaction(KEGG)
Substrate
narbomycin [CPD:C11998];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007];
10-deoxymethymycin [CPD:C11994]
Product
pikromycin [CPD:C11999];
NADP+ [CPD:C00006];
H2O [CPD:C00001];
neopikromycin [CPD:C20739];
novapikromyin [CPD:C20740];
methymycin [CPD:C11996];
neomethymycin [CPD:C11995];
novamethymycin [CPD:C20741]
Comment
A heme-thiolate protein (cytochrome P-450). Involved in the biosynthesis of a number of bacterial macrolide antibiotics containing a desosamine glycoside unit. With narbomycin it hydroxylates at either C-12 to give pikromycin or C-14 to give neopikromycin or both positions to give narvopikromycin. With 10-deoxymethymycin it hydroxylates at either C-10 to give methymycin or C-12 to give neomethymycin or both positions to give novamethymycin.
History
EC 1.14.13.185 created 2014
Pathway
Biosynthesis of 12-, 14- and 16-membered macrolides
Type I polyketide structures
Biosynthesis of secondary metabolites
Orthology
K16006  
pikromycin synthase
Reference
1  [PMID:9831532]
  Authors
Xue Y, Wilson D, Zhao L, Liu Hw, Sherman DH
  Title
Hydroxylation of macrolactones YC-17 and narbomycin is mediated by the pikC-encoded cytochrome P450 in Streptomyces venezuelae.
  Journal
Chem. Biol. 5 (1998) 661-7.
Reference
2  [PMID:16825192]
  Authors
Sherman DH, Li S, Yermalitskaya LV, Kim Y, Smith JA, Waterman MR, Podust LM
  Title
The structural basis for substrate anchoring, active site selectivity, and product formation by P450 PikC from Streptomyces venezuelae.
  Journal
J. Biol. Chem. 281 (2006) 26289-97.
Reference
3  [PMID:19124459]
  Authors
Li S, Ouellet H, Sherman DH, Podust LM
  Title
Analysis of transient and catalytic desosamine-binding pockets in cytochrome P-450 PikC from Streptomyces venezuelae.
  Journal
J. Biol. Chem. 284 (2009) 5723-30.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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