ArticleJournal of the American Chemical Society2012
The substrate-bound crystal structure of a Baeyer-Villiger monooxygenase exhibits a Criegee-like conformation.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed, 97 citations in OpenAlex.
- Unifying and versatile features of flavin-dependent monooxygenases: Diverse catalysis by a common C4a-(hydro)peroxyflavin.The Journal of biological chemistry · 2023Review
- Structural basis of regioselective tryptophan dibromination by the single-component flavin-dependent halogenase AetF.Acta crystallographica. Section D, Structural biology · 2023Article
- A Cold-Active Flavin-Dependent Monooxygenase fromACS catalysis · 2023Article
- Growth-Based, High-Throughput Selection for NADH Preference in an Oxygen-Dependent Biocatalyst.ACS synthetic biology · 2021Article
- In Vivo, High-Throughput Selection of Thermostable Cyclohexanone Monooxygenase (CHMO).Catalysts (Basel, Switzerland) · 2020Article
- Stabilization of cyclohexanone monooxygenase by computational and experimental library design.Biotechnology and bioengineering · 2019Article
- Detoxification Strategies for Zearalenone Using Microorganisms: A Review.Microorganisms · 2019Review
- A Retro-biosynthesis-Based Route to Generate Pinene-Derived Polyesters.Chembiochem : a European journal of chemical biology · 2019Article
- Enzyme Fusions in Biocatalysis: Coupling Reactions by Pairing Enzymes.Chembiochem : a European journal of chemical biology · 2019Review
- Side-Chain Pruning Has Limited Impact on Substrate Preference in a Promiscuous Enzyme.ACS catalysis · 2018Article
- Article
- Improving catalytic activity of the Baeyer-Villiger monooxygenase-based Escherichia coli biocatalysts for the overproduction of (Z)-11-(heptanoyloxy)undec-9-enoic acid from ricinoleic acid.Scientific reports · 2018Article
- Reply to the Comment by Littlechild and Isupov.Microorganisms · 2017Article
- Prospecting Biotechnologically-Relevant Monooxygenases from Cold Sediment Metagenomes: An In Silico Approach.Marine drugs · 2017Article
- Substitution of a Single Amino Acid Reverses the Regiospecificity of the Baeyer-Villiger Monooxygenase PntE in the Biosynthesis of the Antibiotic Pentalenolactone.Biochemistry · 2016Article
- Fluorescent Mechanism-Based Probe for Aerobic Flavin-Dependent Enzyme Activity.Chembiochem : a European journal of chemical biology · 2016Article
- 3'-UTR engineering to improve soluble expression and fine-tuning of activity of cascade enzymes in Escherichia coli.Scientific reports · 2016Article
- Genome mining of the sordarin biosynthetic gene cluster from Sordaria araneosa Cain ATCC 36386: characterization of cycloaraneosene synthase and GDP-6-deoxyaltrose transferase.The Journal of antibiotics · 2016Article
- Engineering of Baeyer-Villiger monooxygenase-based Escherichia coli biocatalyst for large scale biotransformation of ricinoleic acid into (Z)-11-(heptanoyloxy)undec-9-enoic acid.Scientific reports · 2016Article
- Article
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5 authors at 3 institutions in 2 countries.
Funding
Abstract
The Baeyer-Villiger monooxygenases (BVMOs) are a family of bacterial flavoproteins that catalyze the synthetically useful Baeyer-Villiger oxidation reaction. This involves the conversion of ketones into esters or cyclic ketones into lactones by introducing an oxygen atom adjacent to the carbonyl group. The BVMOs offer exquisite regio- and enantiospecificity while acting on a wide range of substrates. They use only NADPH and oxygen as cosubstrates, and produce only NADP(+) and water as byproducts, making them environmentally attractive for industrial purposes. Here, we report the first crystal structure of a BVMO, cyclohexanone monooxygenase (CHMO) from Rhodococcus sp. HI-31 in complex with its substrate, cyclohexanone, as well as NADP(+) and FAD, to 2.4 Å resolution. This structure shows a drastic rotation of the NADP(+) cofactor in comparison to previously reported NADP(+)-bound structures, as the nicotinamide moiety is no longer positioned above the flavin ring. Instead, the substrate, cyclohexanone, is found at this location, in an appropriate position for the formation of the Criegee intermediate. The rotation of NADP(+) permits the substrate to gain access to the reactive flavin peroxyanion intermediate while preventing it from diffusing out of the active site. The structure thus reveals the conformation of the enzyme during the key catalytic step. CHMO is proposed to undergo a series of conformational changes to gradually move the substrate from the solvent, via binding in a solvent excluded pocket that dictates the enzyme's chemospecificity, to a location above the flavin-peroxide adduct where catalysis occurs.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.