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Literature summary for 1.14.14.1 extracted from

  • Lee, S.K.; Basnet, D.B.; Hong, J.S.; Jung, W.S.; Choi, C.Y.; Lee, H.C.; Sohng, J.K.; Ryu, K.G.; Kim, D.J.; Ahn, J.S.; Kim, B.S.; Oh, H.C.; Sherman, D.H.; Yoon, Y.J.
    Structural diversification of macrolactones by substrate-flexible cytochrome P450 monooxygenases (2005), Adv. Synth. Catal., 347, 1369-1378.
No PubMed abstract available

Cloned(Commentary)

Cloned (Comment) Organism
gene pikC, expression of His-tagged enzyme in Escherichia coli strain BL21(DE3) Streptomyces venezuelae

Protein Variants

Protein Variants Comment Organism
additional information construction of an enzyme deletion mutant strain HK954, showing blocked biosynthesis of endogenous macrolactone aglycones Streptomyces venezuelae

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
macrolide YC-17 + [reduced NADPH-hemoprotein reductase] + O2 Streptomyces venezuelae Hydroxylation of C-10 position yield methymycin and of the C-12 neomethymycin. Hydroxylation at both positions yields novamethymycin. methymycin + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
macrolide YC-17 + [reduced NADPH-hemoprotein reductase] + O2 Streptomyces venezuelae Hydroxylation of C-10 position yield methymycin and of the C-12 neomethymycin. Hydroxylation at both positions yields novamethymycin. neomethymycin + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
macrolide YC-17 + [reduced NADPH-hemoprotein reductase] + O2 Streptomyces venezuelae Hydroxylation of C-10 position yield methymycin and of the C-12 neomethymycin. Hydroxylation at both positions yields novamethymycin. novamethymycin + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
additional information Streptomyces venezuelae the enzyme is involved in macrolide biosynthesis and performs unusual C4-hydroxylation ?
-
?
narbomycin + [reduced NADPH-hemoprotein reductase] + O2 Streptomyces venezuelae the organism is a pikromycin producer pikromycin + [oxidized NADPH-hemoprotein reductase] + H2O
-
?

Organism

Organism UniProt Comment Textmining
Streptomyces venezuelae
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strain ATCC 15439
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Purification (Commentary)

Purification (Comment) Organism
recombinant His-tagged PikC from Escherichia coli strain BL21(DE3) by nickel affinity chromatography to homogeneity Streptomyces venezuelae

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
macrolide YC-17 + [reduced NADPH-hemoprotein reductase] + O2 Hydroxylation of C-10 position yield methymycin and of the C-12 neomethymycin. Hydroxylation at both positions yields novamethymycin. Streptomyces venezuelae methymycin + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
macrolide YC-17 + [reduced NADPH-hemoprotein reductase] + O2 Hydroxylation of C-10 position yield methymycin and of the C-12 neomethymycin. Hydroxylation at both positions yields novamethymycin. Streptomyces venezuelae neomethymycin + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
macrolide YC-17 + [reduced NADPH-hemoprotein reductase] + O2 Hydroxylation of C-10 position yield methymycin and of the C-12 neomethymycin. Hydroxylation at both positions yields novamethymycin. Streptomyces venezuelae novamethymycin + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
additional information the enzyme is involved in macrolide biosynthesis and performs unusual C4-hydroxylation Streptomyces venezuelae ?
-
?
additional information structural diversification of macrolactones by the substrate-flexible enzyme, substrate specificity, degree of plasticity towards alternative substrates, overview, modeling of macrolide conformations and enzyme-substrate complex Streptomyces venezuelae ?
-
?
narbomycin + [reduced NADPH-hemoprotein reductase] + O2
-
Streptomyces venezuelae pikromycin + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
narbomycin + [reduced NADPH-hemoprotein reductase] + O2 the organism is a pikromycin producer Streptomyces venezuelae pikromycin + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
oleandomycin + [reduced NADPH-hemoprotein reductase] + O2
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Streptomyces venezuelae 4-hydroxy-oleandomycin + [oxidized NADPH-hemoprotein reductase] + H2O
-
?

Synonyms

Synonyms Comment Organism
cytochrome P450 monooxygenase
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Streptomyces venezuelae
PikC
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Streptomyces venezuelae
PikC hydroxylase
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Streptomyces venezuelae

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
assay at Streptomyces venezuelae

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.2
-
assay at Streptomyces venezuelae

Cofactor

Cofactor Comment Organism Structure
Ferredoxin
-
Streptomyces venezuelae