Reaction: (1) narbomycin + NADPH + H+ + O2 = pikromycin + NADP+ + H2O
(2) narbomycin + NADPH + H+ + O2 = neopikromycin + NADP+ + H2O
(3) narbomycin + 2 NADPH + 2 H+ + 2 O2 = novapikromyin + 2 NADP+ + 2 H2O
(4) 10-deoxymethymycin + NADPH + H+ + O2 = methymycin + NADP+ + H2O
(5) 10-deoxymethymycin + NADPH + H+ + O2 = neomethymycin + NADP+ + H2O
(6) 10-deoxymethymycin + 2 NADPH + 2 H+ + 2 O2 = novamethymycin + 2 NADP+ + 2 H2O
For diagram of reaction click here or click here.
Other name(s): PikC; CYP107L1
Systematic name: narbomycin,NADH:oxygen oxidoreductase (pikromycin-forming)
Comments: 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.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number:
1. Xue, Y., Wilson, D., Zhao, L., Liu Hw and Sherman, D.H. Hydroxylation of macrolactones YC-17 and narbomycin is mediated by the pikC-encoded cytochrome P450 in Streptomyces venezuelae. Chem. Biol. 5 (1998) 661-667. [PMID: 9831532]
2. Sherman, D.H., Li, S., Yermalitskaya, L.V., Kim, Y., Smith, J.A., Waterman, M.R. and Podust, L.M. The structural basis for substrate anchoring, active site selectivity, and product formation by P450 PikC from Streptomyces venezuelae. J. Biol. Chem. 281 (2006) 26289-26297. [PMID: 16825192]
3. Li, S., Ouellet, H., Sherman, D.H. and Podust, L.M. Analysis of transient and catalytic desosamine-binding pockets in cytochrome P-450 PikC from Streptomyces venezuelae. J. Biol. Chem. 284 (2009) 5723-5730. [PMID: 19124459]