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Biocatalytic Properties and Structural Analysis of Eugenol Oxidase from Rhodococcus jostii RHA1: A Versatile Oxidative Biocatalyst.

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Nguyen QT, de Gonzalo G, Binda C, Rioz-Martínez A, Mattevi A, Fraaije MW
OpenAccess logo Chembiochem 17 1359-66 (2016)
Related entries: 5fxd, 5fxe, 5fxf

Cited: 13 times
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Abstract

Eugenol oxidase (EUGO) from Rhodococcus jostii RHA1 had previously been shown to convert only a limited set of phenolic compounds. In this study, we have explored the biocatalytic potential of this flavoprotein oxidase, resulting in a broadened substrate scope and a deeper insight into its structural properties. In addition to the oxidation of vanillyl alcohol and the hydroxylation of eugenol, EUGO can efficiently catalyze the dehydrogenation of various phenolic ketones and the selective oxidation of a racemic secondary alcohol-4-(1-hydroxyethyl)-2-methoxyphenol. EUGO was also found to perform the kinetic resolution of a racemic secondary alcohol. Crystal structures of the enzyme in complexes with isoeugenol, coniferyl alcohol, vanillin, and benzoate have been determined. The catalytic center is a remarkable solvent-inaccessible cavity on the si side of the flavin cofactor. Structural comparison with vanillyl alcohol oxidase from Penicillium simplicissimum highlights a few localized changes that correlate with the selectivity of EUGO for phenolic substrates bearing relatively small p-substituents while tolerating o-methoxy substituents.

Articles - 5fxp mentioned but not cited (3)

  1. Guo Y, Alvigini L, Trajkovic M, Alonso-Cotchico L, Monza E, Savino S, Marić I, Mattevi A, Fraaije MW. Nat Commun 13 7195 (2022)
  2. Shettigar M, Balotra S, Kasprzak A, Pearce SL, Lacey MJ, Taylor MC, Liu JW, Cahill D, Oakeshott JG, Pandey G. Appl Environ Microbiol 86 e00375-20 (2020)
  3. Eggerichs D, Weindorf N, Weddeling HG, Van der Linden IM, Tischler D. Commun Chem 7 123 (2024)


Articles citing this publication (10)

  1. Nguyen QT, Romero E, Dijkman WP, de Vasconcellos SP, Binda C, Mattevi A, Fraaije MW. Biochemistry 57 6209-6218 (2018)
  2. Gygli G, Lucas MF, Guallar V, van Berkel WJH. PLoS Comput Biol 13 e1005787 (2017)
  3. Ewing TA, Gygli G, van Berkel WJ. FEBS J 283 2546-2559 (2016)
  4. Ewing TA, Nguyen QT, Allan RC, Gygli G, Romero E, Binda C, Fraaije MW, Mattevi A, van Berkel WJH. J Biol Chem 292 14668-14679 (2017)
  5. Ewing TA, van Noord A, Paul CE, van Berkel WJH. Molecules 23 E164 (2018)
  6. Habib M, Trajkovic M, Fraaije MW. ACS Catal 8 5549-5552 (2018)
  7. Gandomkar S, Jost E, Loidolt D, Swoboda A, Pickl M, Elaily W, Daniel B, Fraaije MW, Macheroux P, Kroutil W. Adv Synth Catal 361 5264-5271 (2019)
  8. Alvigini L, Gran-Scheuch A, Guo Y, Trajkovic M, Saifuddin M, Fraaije MW, Mattevi A. Chembiochem 22 3225-3233 (2021)
  9. Eggerichs D, Weindorf N, Mascotti ML, Welzel N, Fraaije MW, Tischler D. J Biol Chem 299 104898 (2023)
  10. Christ HA, Daniel NP, Solarczek J, Fresenborg LS, Schallmey A, Menzel H. Appl Microbiol Biotechnol 107 7071-7087 (2023)


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