ArticleThe FEBS journal2009
Structural basis for the erythro-stereospecificity of the L-arginine oxygenase VioC in viomycin biosynthesis.
Article in The FEBS journal, 2009. 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, 70 citations in OpenAlex.
- Discovery and Biosynthesis of the Novel Glycotetrapeptide Antibiotic Biffamycin A.Angewandte Chemie (International ed. in English) · 2026Article
- Mechanistic Insights into Dioxygen Transport Routes in the PHD2 Oxygenase from Long-Time Scale Simulations.Biochemistry · 2026Article
- Three distinct strategies lead to programmable aliphatic C-H oxidation in bicyclomycin biosynthesis.Nature communications · 2025Article
- Identification of Two Distinct Stereoselective Lysine 5-Hydroxylases by Genome Mining Based on Alazopeptin Biosynthetic Enzymes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Probing Ferryl Reactivity in a Nonheme Iron Oxygenase Using an Expanded Genetic Code.ACS catalysis · 2024Article
- Catalytic divergencies in the mechanism of L-arginine hydroxylating nonheme iron enzymes.Frontiers in chemistry · 2024Review
- Oxidative modification of free-standing amino acids by Fe(II)/αKG-dependent oxygenases.Engineering microbiology · 2023Review
- R97 at "Handlebar" Binding Mode in Active Pocket Plays an Important Role in Fe(II)/α-Ketoglutaric Acid-Dependent DioxygenaseMolecules (Basel, Switzerland) · 2023Article
- Functional characterization of a novel violacein biosynthesis operon from Janthinobacterium sp. B9-8.Applied microbiology and biotechnology · 2022Article
- Crystal structure of the α-ketoglutarate-dependent non-heme iron oxygenase CmnC in capreomycin biosynthesis and its engineering to catalyze hydroxylation of the substrate enantiomer.Frontiers in chemistry · 2022Article
- An Iron(IV)-Oxo Intermediate Initiating l-Arginine Oxidation but Not Ethylene Production by the 2-Oxoglutarate-Dependent Oxygenase, Ethylene-Forming Enzyme.Journal of the American Chemical Society · 2021Article
- Anaerobic fixed-target serial crystallography.IUCrJ · 2020Article
- The Desotamide Family of Antibiotics.Antibiotics (Basel, Switzerland) · 2020Review
- Cofactor Generation Cascade for α-Ketoglutarate and Fe(II)-Dependent Dioxygenases.ACS sustainable chemistry & engineering · 2020Article
- Epoxidation Catalyzed by the Nonheme Iron(II)- and 2-Oxoglutarate-Dependent Oxygenase, AsqJ: Mechanistic Elucidation of Oxygen Atom Transfer by a Ferryl Intermediate.Journal of the American Chemical Society · 2020Article
- Genomic analysis of siderophore β-hydroxylases reveals divergent stereocontrol and expands the condensation domain family.Proceedings of the National Academy of Sciences of the United States of America · 2019Article
- Hydrogen Donation but not Abstraction by a Tyrosine (Y68) during Endoperoxide Installation by Verruculogen Synthase (FtmOx1).Journal of the American Chemical Society · 2019Article
- Highly Regioselective and Stereoselective Hydroxylation of Free Amino Acids by a 2-Oxoglutarate-Dependent Dioxygenase fromACS omega · 2019Article
- α-Amine Desaturation of d-Arginine by the Iron(II)- and 2-(Oxo)glutarate-Dependent l-Arginine 3-Hydroxylase, VioC.Biochemistry · 2018Article
- Structural Studies based on two Lysine Dioxygenases with Distinct Regioselectivity Brings Insights Into Enzyme Specificity within the Clavaminate Synthase-Like Family.Scientific reports · 2018Article
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
Abstract
The nonheme iron oxygenase VioC from Streptomyces vinaceus catalyzes Fe(II)-dependent and alpha-ketoglutarate-dependent Cbeta-hydroxylation of L-arginine during the biosynthesis of the tuberactinomycin antibiotic viomycin. Crystal structures of VioC were determined in complexes with the cofactor Fe(II), the substrate L-arginine, the product (2S,3S)-hydroxyarginine and the coproduct succinate at 1.1-1.3 A resolution. The overall structure reveals a beta-helix core fold with two additional helical subdomains that are common to nonheme iron oxygenases of the clavaminic acid synthase-like superfamily. In contrast to other clavaminic acid synthase-like oxygenases, which catalyze the formation of threo diastereomers, VioC produces the erythro diastereomer of Cbeta-hydroxylated L-arginine. This unexpected stereospecificity is caused by conformational control of the bound substrate, which enforces a gauche(-) conformer for chi(1) instead of the trans conformers observed for the asparagine oxygenase AsnO and other members of the clavaminic acid synthase-like superfamily. Additionally, the substrate specificity of VioC was investigated. The side chain of the L-arginine substrate projects outwards from the active site by undergoing interactions mainly with the C-terminal helical subdomain. Accordingly, VioC exerts broadened substrate specificity by accepting the analogs L-homoarginine and L-canavanine for Cbeta-hydroxylation.
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