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Instructions for using Copyright Clearance Center page for details. with the reproduced material. it in a third party non-RSC publication you must and Acinetobacter sp. the Open University "Reproduced from" can be substituted with "Adapted from". and Jisc. This may take some time to load. article provided that the correct acknowledgement is given with the reproduced material. Baeyer-Villiger monooxygenases: From protein engineering to biocatalytic applications. contained in this article in third party publications Biocatalytic Oxidation Reactions: A Chemist's Perspective. If you are not the author of this article and you wish to reproduce material from A Retro‐biosynthesis‐Based Route to Generate Pinene‐Derived Polyesters. The OTEMO wild‐type enzyme converted (−)‐1 into an equal (50:50) mixture of the normal and abnormal products. Efficient Synthesis of Methyl 3-Acetoxypropionate by a Newly Identified Baeyer-Villiger Monooxygenase. Learn about our remote access options, Department of Biotechnology and Enzyme Catalysis, Institute of Biochemistry, Universität Greifswald, Felix-Hausdorff-Strasse 4, 17487 Greifswald, Germany. The regioselectivity of the Baeyer-Villiger monooxygenase-catalyzed oxidation is governed mostly by electronic effects leading to the migration of the higher substituted residue. Same Substrate, Many Reactions: Oxygen Activation in Flavoenzymes. Exploring the Substrate Scope of Baeyer–Villiger Monooxygenases with Branched Lactones as Entry towards Polyesters. Such materials are peer reviewed and may be re‐organized for online delivery, but are not copy‐edited or typeset. In Vivo, High-Throughput Selection of Thermostable Cyclohexanone Monooxygenase (CHMO). As a service to our authors and readers, this journal provides supporting information supplied by the authors. In all cases the Ref. The high reactivity and regioselectivity of ketone R 1 and R 2 towards the lactones P 1 and P 3 by the B V reaction, has been studied using DFT methods at the B3LYP/6-31G(d). or in a thesis or dissertation provided that the correct acknowledgement is given If you are the author of this article you do not need to formally request permission The regioselectivity of the Baeyer–Villiger oxidation of norbornan-7-ones can be steered by the distal 2-endo-substituents present.Hydrolysis of the resulting bicyclic lactones provides a stereospecific route to functionalized cyclohexanes. . We investigated the regioselectivity of 2‐oxo‐Δ3‐4,5,5‐trimethylcyclopentenylacetyl‐CoA monooxygenase from Pseudomonas putida (OTEMO) for cis‐bicyclo[3.2.0]hept‐2‐en‐6‐one (1) and trans‐dihydrocarvone (2), and we were able to switch the regioselectivity of this enzyme for one of the substrate enantiomers. This study indicates that there are … Authors contributing to RSC publications (journal articles, books or book chapters) Information about reproducing material from RSC articles with different licences and you may need to create a new Wiley Online Library account. Type II flavoprotein monooxygenase PsFMO_A from the bacterium Pimelobacter sp. Request. to access the full features of the site or access our, Instructions for using Copyright Clearance Center page. Hydrolysis of the resulting bicyclic lactones provides a stereospecific route to functionalized cyclohexanes. Finding the hot spot: The regioselectivity of the Baeyer–Villiger monooxygenase (BVMO) 2‐oxo‐Δ3‐4,5,5‐trimethylcyclopentenylacetyl‐CoA monooxygenase for (−)‐cis‐bicyclo[3.2.0]hept‐2‐en‐6‐one is controlled by mutation of the active‐site residues to smaller amino acids, so that both regioisomeric products are accessible. Baeyer-Villiger Oxidation. The Baeyer-Villiger Oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which converts ketones to esters and cyclic ketones to lactones. When the substituent at C(3) is a MeO or (tBu)Me2SiO group, the Baeyer-Villiger oxidation leads to 3,8-dioxabicyclo[3.2.1]octan-2-ones due to preferred C(3) migration. Reproduced material should be attributed as follows: If the material has been adapted instead of reproduced from the original RSC publication citation, Infoscience - École polytechnique fédérale de Lausanne, Update/Correction/Removal New 3-oxy substituted and 3,6-dioxydisubstituted 7-oxabicyclo[2.2.1]heptan-2-ones have been prepared. Learn more. Request. the whole article in a third party publication with the exception of reproduction Baeyer-Villiger monooxygenases: tunable oxidative biocatalysts. Discover our research outputs and cite our work. From Bugs to Bioplastics: Total (+)‐Dihydrocarvide Biosynthesis by Engineered Escherichia coli. Theoretical Study on the Regioselectivity of Baeyer−Villiger Reaction of α‑Me‑,-F‑, -CF 3‑Cyclohexanones Yoshimitsu Itoh,† Masahiro Yamanaka,‡ and Koichi Mikami* Department of Applied Chemistry, Tokyo Institute of Technology, Tokyo 152-8552, Japan * S Supporting Information ABSTRACT: The origin of the regioselectivity of the Working off-campus? Side-Chain Pruning Has Limited Impact on Substrate Preference in a Promiscuous Enzyme. This study indicates that there are hot spots in the active site of BVMOs that are important for controlling the regioselectivity. To submit an update or takedown request for this paper, please submit an Update/Correction/Removal The Baeyer-Villiger can be carried out with peracids, such as MCBPA, or … If the substituent at C(3-exo) is an O-acyl or another group less electron-releasing, the bridgehead C(1) migration is favoured, leading to 2,8-dioxa-bicyclo[3.2.1]octan-3-ones. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. of the whole article in a thesis or dissertation. Hot spots for the protein engineering of Baeyer-Villiger monooxygenases, cbic201700223-sup-0001-misc_information.pdf.
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