ArticleThe Journal of biological chemistry2012
Substrate recognition by the multifunctional cytochrome P450 MycG in mycinamicin hydroxylation and epoxidation reactions.
Article in The Journal of biological chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.
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Who cites it
34 citing papers in PubMed, 73 citations in OpenAlex.
- Clock-Turning Control of P450 TxtE Regioselectivity Enables Precise Site Functionalization of Aromatic Compounds.JACS Au · 2026Article
- Exploring extreme environments in Türkiye for novel P450s through metagenomic analysis.PloS one · 2025Article
- Mce1R of Mycobacterium tuberculosis prefers long-chain fatty acids as specific ligands: a computational study.Molecular diversity · 2023Article
- Structure-Function Analysis of the Biotechnologically Important Cytochrome P450 107 (CYP107) Enzyme Family.Biomolecules · 2023Article
- Conformational heterogeneity suggests multiple substrate binding modes in CYP106A2.Journal of inorganic biochemistry · 2023Article
- Crystal Structure and Biochemical Analysis of a Cytochrome P450 Steroid Hydroxylase (Journal of microbiology and biotechnology · 2023Article
- Engineering sequence and selectivity of late-stage C-H oxidation in the MycG iterative cytochrome P450.Journal of industrial microbiology & biotechnology · 2022Article
- Article
- High ResolutionFrontiers in molecular biosciences · 2022Review
- Ribosome-binding and anti-microbial studies of the mycinamicins, 16-membered macrolide antibiotics from Micromonospora griseorubida.Nucleic acids research · 2021Article
- Characterization of high-HIUCrJ · 2021Article
- A dynamic understanding of cytochrome P450 structure and function through solution NMR.Current opinion in biotechnology · 2021Review
- An overview of the cytochrome P450 enzymes that catalyze the same-site multistep oxidation reactions in biotechnologically relevant selected actinomycete strains.Applied microbiology and biotechnology · 2021Review
- Molecular Basis of Iterative C─H Oxidation by TamI, a Multifunctional P450 monooxygenase from the Tirandamycin Biosynthetic Pathway.ACS catalysis · 2020Article
- (+)-Sesamin-oxidising CYP92B14 shapes specialised lignan metabolism in sesame.The Plant journal : for cell and molecular biology · 2020Article
- Computational-Based Mechanistic Study and Engineering of Cytochrome P450 MycG for Selective Oxidation of 16-Membered Macrolide Antibiotics.Journal of the American Chemical Society · 2020Article
- Flavin-Dependent Monooxygenases NotI and NotI' Mediate Spiro-Oxindole Formation in Biosynthesis of the Notoamides.Chembiochem : a European journal of chemical biology · 2020Article
- What Your Crystal Structure Will Not Tell You about Enzyme Function.Accounts of chemical research · 2019Article
- Some Surprising Implications of NMR-directed Simulations of Substrate Recognition and Binding by Cytochrome P450Journal of molecular biology · 2018Article
- Heterologous pathway assembly reveals molecular steps of fungal terreic acid biosynthesis.Scientific reports · 2018Article
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Authors and funding
9 authors at 6 institutions in 3 countries.
Funding
Abstract
The majority of characterized cytochrome P450 enzymes in actinomycete secondary metabolic pathways are strictly substrate-, regio-, and stereo-specific. Examples of multifunctional biosynthetic cytochromes P450 with broader substrate and regio-specificity are growing in number and are of particular interest for biosynthetic and chemoenzymatic applications. MycG is among the first P450 monooxygenases characterized that catalyzes both hydroxylation and epoxidation reactions in the final biosynthetic steps, leading to oxidative tailoring of the 16-membered ring macrolide antibiotic mycinamicin II in the actinomycete Micromonospora griseorubida. The ordering of steps to complete the biosynthetic process involves a complex substrate recognition pattern by the enzyme and interplay between three tailoring modifications as follows: glycosylation, methylation, and oxidation. To understand the catalytic properties of MycG, we structurally characterized the ligand-free enzyme and its complexes with three native metabolites. These include substrates mycinamicin IV and V and their biosynthetic precursor mycinamicin III, which carries the monomethoxy sugar javose instead of the dimethoxylated sugar mycinose. The two methoxy groups of mycinose serve as sensors that mediate initial recognition to discriminate between closely related substrates in the post-polyketide oxidative tailoring of mycinamicin metabolites. Because x-ray structures alone did not explain the mechanisms of macrolide hydroxylation and epoxidation, paramagnetic NMR relaxation measurements were conducted. Molecular modeling based on these data indicates that in solution substrate may penetrate the active site sufficiently to place the abstracted hydrogen atom of mycinamicin IV within 6 Å of the heme iron and ~4 Å of the oxygen of iron-ligated water.
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