4b7d

Structural highlights

Function

PIKC_STRVZ Catalyzes the hydroxylation of narbomycin to give rise to pikromycin, and of 10-deoxymethymycin (YC-17) to give rise to methymycin and neomethymycin during macrolide antibiotic biosynthesis. In addition, produces low amounts of neopicromycin, novapikromycin and novamethymycin. Requires the participation of a ferredoxin and a ferredoxin reductase for the transfer of electrons from NADPH to the monooxygenase.^{[1] [2] [3] [4] [5] [6]}

See Also

• Cytochrome P450 hydroxylase 3D structures

References

1. ↑ Sherman DH, Li S, Yermalitskaya LV, Kim Y, Smith JA, Waterman MR, Podust LM. The structural basis for substrate anchoring, active site selectivity, and product formation by P450 PikC from Streptomyces venezuelae. J Biol Chem. 2006 Sep 8;281(36):26289-97. Epub 2006 Jul 6. PMID:16825192 doi:10.1074/jbc.M605478200
2. ↑ Li S, Ouellet H, Sherman DH, Podust LM. Analysis of transient and catalytic desosamine-binding pockets in cytochrome P-450 PikC from Streptomyces venezuelae. J Biol Chem. 2009 Feb 27;284(9):5723-30. Epub 2009 Jan 4. PMID:19124459 doi:10.1074/jbc.M807592200
3. ↑ Li S, Chaulagain MR, Knauff AR, Podust LM, Montgomery J, Sherman DH. Selective oxidation of carbolide C-H bonds by an engineered macrolide P450 mono-oxygenase. Proc Natl Acad Sci U S A. 2009 Oct 15. PMID:19833867
4. ↑ Negretti S, Narayan AR, Chiou KC, Kells PM, Stachowski JL, Hansen DA, Podust LM, Montgomery J, Sherman DH. Directing Group-Controlled Regioselectivity in an Enzymatic C-H Bond Oxygenation. J Am Chem Soc. 2014 Mar 21. PMID:24627965 doi:http://dx.doi.org/10.1021/ja5016052
5. ↑ Betlach MC, Kealey JT, Ashley GW, McDaniel R. Characterization of the macrolide P-450 hydroxylase from Streptomyces venezuelae which converts narbomycin to picromycin. Biochemistry. 1998 Oct 20;37(42):14937-42. PMID:9778370 doi:10.1021/bi981699c
6. ↑ Xue Y, Wilson D, Zhao L, Liu Hw, Sherman DH. Hydroxylation of macrolactones YC-17 and narbomycin is mediated by the pikC-encoded cytochrome P450 in Streptomyces venezuelae. Chem Biol. 1998 Nov;5(11):661-7. PMID:9831532 doi:10.1016/s1074-5521(98)90293-9