Parent Class:

EC-Numbers → 1 -- Oxidoreductases → 1.14 -- Acting on paired donors, with incorporation or reduction of molecular oxygen → 1.14.15 -- With a reduced iron-sulfur protein as one donor, and incorporation of one atom of oxygen into the other donor

Synonyms: PikC, CYP107L1

Systematic Name: narbomycin,reduced ferredoxin:oxygen oxidoreductase (pikromycin-forming)

Unification Links: BRENDA:1.14.15.33, ENZYME:1.14.15.33, IUBMB-ExplorEnz:1.14.15.33

Supersedes EC number: 1.14.13.185

Reaction:
10-deoxymethymycin + 2 reduced ferredoxin [iron-sulfur] cluster + dioxygen + 2 H⁺ → methymycin + 2 oxidized ferredoxin [iron-sulfur] cluster + H₂O,
narbomycin + 2 reduced ferredoxin [iron-sulfur] cluster + dioxygen + 2 H⁺ → neopikromycin + 2 oxidized ferredoxin [iron-sulfur] cluster + H₂O,
methymycin + 2 reduced ferredoxin [iron-sulfur] cluster + dioxygen + 2 H⁺ → novamethymycin + 2 oxidized ferredoxin [iron-sulfur] cluster + H₂O,
neomethymycin + 2 reduced ferredoxin [iron-sulfur] cluster + dioxygen + 2 H⁺ → novamethymycin + 2 oxidized ferredoxin [iron-sulfur] cluster + H₂O,
10-deoxymethymycin + 2 reduced ferredoxin [iron-sulfur] cluster + dioxygen + 2 H⁺ → neomethymycin + 2 oxidized ferredoxin [iron-sulfur] cluster + H₂O,
pikromycin + 2 reduced ferredoxin [iron-sulfur] cluster + dioxygen + 2 H⁺ → novapikromycin + 2 oxidized ferredoxin [iron-sulfur] cluster + H₂O,
narbomycin + 2 reduced ferredoxin [iron-sulfur] cluster + dioxygen + 2 H⁺ → pikromycin + 2 oxidized ferredoxin [iron-sulfur] cluster + H₂O,
neopikromycin + 2 reduced ferredoxin [iron-sulfur] cluster + dioxygen + 2 H⁺ → novapikromycin + 2 oxidized ferredoxin [iron-sulfur] cluster + H₂O

Summary:
A cytochrome P-450 (heme-thiolate) protein. Involved in the biosynthesis of a number of bacterial macrolide antibiotics contaiing a desosamine glycoside unit. With 10-deoxymethymycin it hydroxylates at either C-10 to give methymycin or C-12 to give neomethymycin.

Citations: [Xue98b, Sherman06, Li09h]

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References

Li09h: Li S, Ouellet H, Sherman DH, Podust LM (2009). "Analysis of transient and catalytic desosamine-binding pockets in cytochrome P-450 PikC from Streptomyces venezuelae." J Biol Chem 284(9);5723-30. PMID: 19124459

Sherman06: Sherman DH, Li S, Yermalitskaya LV, Kim Y, Smith JA, Waterman MR, Podust LM (2006). "The structural basis for substrate anchoring, active site selectivity, and product formation by P450 PikC from Streptomyces venezuelae." J Biol Chem 281(36);26289-97. PMID: 16825192

Xue98b: Xue Y, Wilson D, Zhao L, Liu Hw, Sherman DH (1998). "Hydroxylation of macrolactones YC-17 and narbomycin is mediated by the pikC-encoded cytochrome P450 in Streptomyces venezuelae." Chem Biol 5(11);661-7. PMID: 9831532

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 46(D1):D633-D639 2018
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