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Characterization and Crystal Structure of a Robust Cyclohexanone Monooxygenase.

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Romero E, Castellanos JR, Mattevi A, Fraaije MW
OpenAccess logo Angew Chem Int Ed Engl 55 15852-15855 (2016)
Cited: 29 times
EuropePMC logo PMID: 27873437

Abstract

Cyclohexanone monooxygenase (CHMO) is a promising biocatalyst for industrial reactions owing to its broad substrate spectrum and excellent regio-, chemo-, and enantioselectivity. However, the low stability of many Baeyer-Villiger monooxygenases is an obstacle for their exploitation in industry. Characterization and crystal structure determination of a robust CHMO from Thermocrispum municipale is reported. The enzyme efficiently converts a variety of aliphatic, aromatic, and cyclic ketones, as well as prochiral sulfides. A compact substrate-binding cavity explains its preference for small rather than bulky substrates. Small-scale conversions with either purified enzyme or whole cells demonstrated the remarkable properties of this newly discovered CHMO. The exceptional solvent tolerance and thermostability make the enzyme very attractive for biotechnology.

Articles - 5m10 mentioned but not cited (4)

  1. Overriding Traditional Electronic Effects in Biocatalytic Baeyer-Villiger Reactions by Directed Evolution. Li G, Garcia-Borràs M, Fürst MJLJ, Ilie A, Fraaije MW, Houk KN, Reetz MT. J Am Chem Soc 140 10464-10472 (2018)
  2. Discovery of Two Native Baeyer-Villiger Monooxygenases for Asymmetric Synthesis of Bulky Chiral Sulfoxides. Zhang Y, Liu F, Xu N, Wu YQ, Zheng YC, Zhao Q, Lin G, Yu HL, Xu JH. Appl Environ Microbiol 84 e00638-18 (2018)
  3. Side-Chain Pruning Has Limited Impact on Substrate Preference in a Promiscuous Enzyme. Fürst MJLJ, Romero E, Gómez Castellanos JR, Fraaije MW, Mattevi A. ACS Catal 8 11648-11656 (2018)
  4. Bioinformatic Mining and Structure-Activity Profiling of Baeyer-Villiger Monooxygenases from Mycobacterium tuberculosis. Tomas N, Leonelli D, Campoy M, Marthey S, Le NH, Rengel D, Martin V, Pál A, Korduláková J, Eynard N, Guillet V, Mourey L, Daffé M, Lemassu A, André G, Marrakchi H. mSphere 7 e0048221 (2022)


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  1. Toward Upscaled Biocatalytic Preparation of Lactone Building Blocks for Polymer Applications. Delgove MAF, Elford MT, Bernaerts KV, Wildeman SMA. Org Process Res Dev 22 803-812 (2018)
  2. Design of fusion enzymes for biocatalytic applications in aqueous and non-aqueous media. Ma Y, Zhang N, Vernet G, Kara S. Front Bioeng Biotechnol 10 944226 (2022)

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  1. Ancestral-sequence reconstruction unveils the structural basis of function in mammalian FMOs. Nicoll CR, Bailleul G, Fiorentini F, Mascotti ML, Fraaije MW, Mattevi A. Nat Struct Mol Biol 27 14-24 (2020)
  2. Controlling the Regioselectivity of Baeyer-Villiger Monooxygenases by Mutation of Active-Site Residues. Balke K, Bäumgen M, Bornscheuer UT. Chembiochem 18 1627-1638 (2017)
  3. Kinetic insights into ϵ-caprolactone synthesis: Improvement of an enzymatic cascade reaction. Scherkus C, Schmidt S, Bornscheuer UT, Gröger H, Kara S, Liese A. Biotechnol Bioeng 114 1215-1221 (2017)
  4. Stabilization of cyclohexanone monooxygenase by computational and experimental library design. Fürst MJLJ, Boonstra M, Bandstra S, Fraaije MW. Biotechnol Bioeng 116 2167-2177 (2019)
  5. Mining the Genome of Streptomyces leeuwenhoekii: Two New Type I Baeyer-Villiger Monooxygenases From Atacama Desert. Gran-Scheuch A, Trajkovic M, Parra L, Fraaije MW. Front Microbiol 9 1609 (2018)
  6. Manipulating the stereoselectivity of the thermostable Baeyer-Villiger monooxygenase TmCHMO by directed evolution. Li G, Fürst MJLJ, Mansouri HR, Ressmann AK, Ilie A, Rudroff F, Mihovilovic MD, Fraaije MW, Reetz MT. Org Biomol Chem 15 9824-9829 (2017)
  7. Crystal structure of pyrrolizidine alkaloid N-oxygenase from the grasshopper Zonocerus variegatus. Kubitza C, Faust A, Gutt M, Gäth L, Ober D, Scheidig AJ. Acta Crystallogr D Struct Biol 74 422-432 (2018)
  8. A Prospective Life Cycle Assessment (LCA) of Monomer Synthesis: Comparison of Biocatalytic and Oxidative Chemistry. Delgove MAF, Laurent AB, Woodley JM, De Wildeman SMA, Bernaerts KV, van der Meer Y. ChemSusChem 12 1349-1360 (2019)
  9. Evolution of enzyme functionality in the flavin-containing monooxygenases. Bailleul G, Yang G, Nicoll CR, Mattevi A, Fraaije MW, Mascotti ML. Nat Commun 14 1042 (2023)
  10. Exploring the Substrate Scope of Baeyer-Villiger Monooxygenases with Branched Lactones as Entry towards Polyesters. Delgove MAF, Fürst MJLJ, Fraaije MW, Bernaerts KV, De Wildeman SMA. Chembiochem 19 354-360 (2018)
  11. Fungal BVMOs as alternatives to cyclohexanone monooxygenase. Mthethwa KS, Kassier K, Engel J, Kara S, Smit MS, Opperman DJ. Enzyme Microb Technol 106 11-17 (2017)
  12. 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. Woo JM, Jeon EY, Seo EJ, Seo JH, Lee DY, Yeon YJ, Park JB. Sci Rep 8 10280 (2018)
  13. Mutations Increasing Cofactor Affinity, Improve Stability and Activity of a Baeyer-Villiger Monooxygenase. Mansouri HR, Gracia Carmona O, Jodlbauer J, Schweiger L, Fink MJ, Breslmayr E, Laurent C, Feroz S, P Goncalves LC, Rial DV, Mihovilovic MD, Bommarius AS, Ludwig R, Oostenbrink C, Rudroff F. ACS Catal 12 11761-11766 (2022)
  14. Escherichia coli Fails to Efficiently Maintain the Activity of an Important Flavin Monooxygenase in Recombinant Overexpression. Milker S, Goncalves LCP, Fink MJ, Rudroff F. Front Microbiol 8 2201 (2017)
  15. Enantioselective sulfoxidation using Streptomyces glaucescens GLA.0. Salama S, Dishisha T, Habib MH, Abdelazem AZ, Bakeer W, Abdel-Latif M, Gaber Y. RSC Adv 10 32335-32344 (2020)
  16. The Unexplored Importance of Fleeting Chiral Intermediates in Enzyme-Catalyzed Reactions. Reetz MT, Garcia-Borràs M. J Am Chem Soc 143 14939-14950 (2021)
  17. Alternative Splicing of the Aflatoxin-Associated Baeyer⁻Villiger Monooxygenase from Aspergillus flavus: Characterisation of MoxY Isoforms. Tolmie C, Smit MS, Opperman DJ. Toxins (Basel) 10 E521 (2018)
  18. Crystal structures of the isochorismatase domains from Vibrio anguillarum. Du J, Deng T, Ma Q. Biochem Biophys Res Commun 490 827-833 (2017)
  19. Efficient Synthesis of Methyl 3-Acetoxypropionate by a Newly Identified Baeyer-Villiger Monooxygenase. Liu YY, Li CX, Xu JH, Zheng GW. Appl Environ Microbiol 85 e00239-19 (2019)
  20. A concise and scalable chemoenzymatic synthesis of prostaglandins. Yin Y, Wang J, Li J. Nat Commun 15 2523 (2024)
  21. In Vivo, High-Throughput Selection of Thermostable Cyclohexanone Monooxygenase (CHMO). Maxel S, Zhang L, King E, Acosta AP, Luo R, Li H. Catalysts 10 935 (2020)
  22. Multi-stage nuclear transcriptomic insights of morphogenesis and biparental role changes in Lentinula edodes. Song X, Chen M, Zhao Y, Zhang M, Zhang L, Zhang D, Song C, Shang X, Tan Q. Appl Microbiol Biotechnol 107 5469-5489 (2023)
  23. Nature stays natural: two novel chemo-enzymatic one-pot cascades for the synthesis of fragrance and flavor aldehydes. Giparakis S, Winkler M, Rudroff F. Green Chem 26 1338-1344 (2024)


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