Colorimetric High-Throughput Screening Method for Directed Evolution of Prazole Sulfide Monooxygenase.
Baeyer-Villiger monooxygenase
biocatalysis
directed evolution
high-throughput screening
proton pump inhibitors
Journal
Chembiochem : a European journal of chemical biology
ISSN: 1439-7633
Titre abrégé: Chembiochem
Pays: Germany
ID NLM: 100937360
Informations de publication
Date de publication:
17 08 2022
17 08 2022
Historique:
revised:
27
05
2022
received:
20
04
2022
pubmed:
1
6
2022
medline:
20
8
2022
entrez:
31
5
2022
Statut:
ppublish
Résumé
Baeyer-Villiger monooxygenases (BVMOs) are important biocatalysts for the enzymatic synthesis of chiral sulfoxides, including chiral sulfoxide-type proton pump inhibitors for the treatment of gastrointestinal diseases. However, native BVMOs are not yet suitable for practical application due to their unsatisfactory activity and thermostability. Although protein engineering approaches can help address these issues, few feasible high-throughput methods are available for the engineering of such enzymes. Herein, a colorimetric detection method to distinguish sulfoxides from sulfides and sulfones was developed for prazole sulfide monooxygenases. Directed evolution enabled by this method has identified a prazole sulfide monooxygenase CbBVMO variant with improved activity and thermostability that catalyzes the asymmetric oxidation of lansoprazole sulfide. A 71.3 % increase in conversion and 6 °C enhancement in the melting point were achieved compared with the wild-type enzyme. This new method is feasible for high-throughput screening of prazole sulfide monooxygenase variants with improved activity, thermostability, and/or substrate specificity.
Identifiants
pubmed: 35639013
doi: 10.1002/cbic.202200228
doi:
Substances chimiques
Sulfides
0
Sulfoxides
0
Mixed Function Oxygenases
EC 1.-
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202200228Informations de copyright
© 2022 Wiley-VCH GmbH.
Références
A. Baeyer, V. Villiger, Ber. Dtsch. Chem. Ges. 1899, 32, 3625-3633.
G. de Gonzalo, M. W. Fraaije, ChemCatChem 2013, 5, 403-415.
G. de Gonzalo, M. J. L. J. Fürst, M. W. Fraaije, Catalysts 2017, 7, 288.
Y. J. Hu, W. H. Xu, C. G. Hui, J. Xu, M. L. Huang, X. F. Lin, Q. Wu, Chem. Commun. 2020, 56, 9356-9359.
B. Skrzydło-Radomańska, P. Radwan, Prz Gastroenterol. 2015, 10, 191-196.
F. Liu, C. Shou, Q. Geng, C. Zhao, H. L. Yu, J. H. Xu, Appl. Microbiol. Biotechnol. 2021, 105, 3169-3180.
Y. Zhang, Y. Q. Wu, N. Xu, Q. Zhao, H. L. Yu, J. H. Xu, ACS Sustainable Chem. Eng. 2019, 7, 7218-7226.
Y. K. Bong, S. Song, J. Nazor, M. Vogel, M. Widegren, D. Smith, S. J. Collier, R. Wilson, S. M. Palanivel, K. Narayanaswamy, B. Mijts, M. D. Clay, R. Fong, J. Colbeck, A. Appaswami, S. Muley, J. Zhu, X. Zhang, J. Liang, D. Entwistle, J. Org. Chem. 2018, 83, 7453-7458.
S. M. Ren, F. Liu, Y. Q. Wu, Q. Chen, Z. J. Zhang, H. L. Yu, J. H. Xu, Biotechnol. Bioeng. 2021, 118, 737-744.
P. Zhao, S. M. Ren, F. Liu, Y. C. Zheng, N. Xu, J. Pan, H. L. Yu, J. H. Xu, J. Mol. Catal. 2021, 509, 111625.
P. Santner, L. K. Szabó, S. N. Chanquia, A. H. Merrild, F. Hollmann, S. Kara, B. E. Eser, ChemCatChem 2021, 13, 4038-4046.
K. Balke, M. Bäumgen, U. T. Bornscheuer, ChemBioChem 2017, 18, 1627-1638.
C. Ren, X. Wen, J. Mencius, S. Quan, Bioresour. Bioprocess. 2019, 6, 53.
H. L. Van Beek, E. Romero, M. W. Fraaije, ACS Chem. Biol. 2017, 12, 291-299.
Y. J. Li, Y. C. Zheng, Q. Geng, F. Liu, Z. J. Zhang, J. H. Xu, H. L. Yu, Bioresour. Bioprocess. 2021, 8, 81.
H. F. Xu, W. N. Liang, L. L. Ning, Y. Y. Jiang, W. X. Yang, C. Wang, F. F. Qi, L. Ma, L. Du, L. Fourage, Y. J. Zhou, S. Y. Li, ChemCatChem 2019, 12, 80-84.
A. Kirschner, U. T. Bornscheuer, Appl. Microbiol. Biotechnol. 2008, 81, 465-472.
S. Saß, M. Kadow, K. Geitner, M. L. Thompson, L. Talmann, D. Böttcher, M. Schmidt, U. T. Bornscheuer, Tetrahedron 2012, 68, 7575-7580.
M. C. Gutiérrez, A. Sleegers, H. D. Simpson, V. Alphand, R. Furstoss, Org. Biomol. Chem. 2003, 1, 3500-3506.
R. Sicard, L. S. Chen, A. J. Marsaioli, J. L. Reymond, Adv. Synth. Catal. 2005, 347, 1041-1050.
J. Roberts, M. L. Mcnaughtan, J. Maclachlan, C. Hunter, O. Pahl, Rapid Commun. Mass Spectrom. 2018, 32, 929-941.
G. Shankar, R. M. Borkar, U. Suresh, M. Kanakaraju, G. Saicharan, S. Misra, R. Srinivas, New J. Chem. 2019, 43, 7294-7306.
M. DellaGreca, M. R. Iesce, L. Previtera, M. Rubino, F. Temussi, M. Brigante, Chemosphere 2006, 63, 1087-1093.
J. Shainsky, N. L. Derry, Y. Leichtmann-Bardoogo, T. K. Wood, A. Fishman, Appl. Environ. Microbiol. 2009, 75, 4711-4719.
J. Jumper, R. Evans, A. Pritzel, T. Green, M. Figurnov, O. Ronneberger, K. Tunyasuvunakool, R. Bates, A. Zidek, A. Potapenko, A. Bridgland, C. Meyer, S. A. A. Kohl, A. J. Ballard, A. Cowie, B. Romera-Paredes, S. Nikolov, R. Jain, J. Adler, T. Back, S. Petersen, D. Reiman, E. Clancy, M. Zielinski, M. Steinegger, M. Pacholska, T. Berghammer, S. Bodenstein, D. Silver, O. Vinyals, A. W. Senior, K. Kavukcuoglu, P. Kohli, D. Hassabis, Nature 2021, 596, 583-589.
S. Bordewick, A. Beier, K. Balke, U. T. Bornscheuer, Enzyme Microb. Technol. 2018, 109, 31-42.
G. Qu, A. Li, C. G. Acevedo-Rocha, Z. Sun, M. T. Reetz, Angew. Chem. Int. Ed. 2020, 59, 13204-13231;
Angew. Chem. 2020, 132, 13304-13333.
F. Forneris, R. Orru, D. Bonivento, L. R. Chiarelli, A. Mattevi, FEBS J. 2009, 276, 2833-2840.
H. W. Jiang, Q. Chen, J. Pan, G. W. Zheng, J. H. Xu, Appl. Biochem. Biotechnol. 2020, 192, 530-543.