KEGG   ENZYME: 1.14.15.33Help
Entry
EC 1.14.15.33               Enzyme                                 

Name
pikromycin synthase;
PikC;
CYP107L1
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced iron-sulfur protein as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
narbomycin,reduced ferredoxin:oxygen oxidoreductase (pikromycin-forming)
Reaction(IUBMB)
(1) narbomycin + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = pikromycin + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O [RN:R06464];
(2) narbomycin + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = neopikromycin + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O [RN:R10626];
(3) narbomycin + 4 reduced ferredoxin [iron-sulfur] cluster + 4 H+ + 2 O2 = novapikromyin + 4 oxidized ferredoxin [iron-sulfur] cluster + 2 H2O [RN:R10627];
(4) 10-deoxymethymycin + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = methymycin + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O [RN:R06463];
(5) 10-deoxymethymycin + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = neomethymycin + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O [RN:R06462];
(6) 10-deoxymethymycin + 4 reduced ferredoxin [iron-sulfur] cluster + 4 H+ + 2 O2 = novamethymycin + 4 oxidized ferredoxin [iron-sulfur] cluster + 2 H2O [RN:R10628]
Reaction(KEGG)
Substrate
narbomycin [CPD:C11998];
reduced ferredoxin [iron-sulfur] cluster [CPD:C00138];
H+ [CPD:C00080];
O2 [CPD:C00007];
10-deoxymethymycin [CPD:C11994]
Product
pikromycin [CPD:C11999];
oxidized ferredoxin [iron-sulfur] cluster [CPD:C00139];
H2O [CPD:C00001];
neopikromycin [CPD:C20739];
novapikromyin;
methymycin [CPD:C11996];
neomethymycin [CPD:C11995];
novamethymycin [CPD:C20741]
Comment
A cytochrome P-450 (heme-thiolate) protein. 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 1.14.15.33 created 2014 as EC 1.14.13.185, transferred 2018 to EC 1.14.15.33
Pathway
ec00522  Biosynthesis of 12-, 14- and 16-membered macrolides
ec01100  Metabolic pathways
ec01130  Biosynthesis of antibiotics
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 5:661-7 (1998)
DOI:10.1016/S1074-5521(98)90293-9
  Sequence
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 281:26289-97 (2006)
DOI:10.1074/jbc.M605478200
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 284:5723-30 (2009)
DOI:10.1074/jbc.M807592200
Other DBs
ExplorEnz - The Enzyme Database: 1.14.15.33
IUBMB Enzyme Nomenclature: 1.14.15.33
ExPASy - ENZYME nomenclature database: 1.14.15.33
BRENDA, the Enzyme Database: 1.14.15.33

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