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A Regio‐ and Stereoselective ω‐Transaminase/Monoamine Oxidase Cascade for the Synthesis of Chiral 2,5‐Disubstituted Pyrrolidines
Open accessAbstract
Biocatalytic approaches to the synthesis of optically pure chiral amines, starting from simple achiral building blocks, are highly desirable because such motifs are present in a wide variety of important natural products and pharmaceutical compounds. Herein, a novel one‐pot ω‐transaminase (TA)/monoamine oxidase (MAO‐N) cascade process for the synthesis of chiral 2,5‐disubstituted pyrrolidines is reported. The reactions proceeded with excellent enantio‐ and diastereoselectivity (>94 % ee; >98 % de) and can be performed on a preparative scale. This methodology exploits the complementary regio‐ and stereoselectivity displayed by both enzymes, which ensures that the stereogenic center established by the transaminase is not affected by the monoamine oxidase, and highlights the potential of this multienzyme cascade for the efficient synthesis of chiral building blocks.
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Citations
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Directed evolution drives the next generation of biocatalysts
Turner, N. J. (2009) · Nature Chemical Biology · doi:10.1038/nchembio.203 · Cited by 785
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Cited by
Wu, X., Ge, J., Yang, C., Hou, M., & Liu, Z. (2015) · Chemical Communications · doi:10.1039/c5cc05136c · Cited by 553
Hu, L., Lin, L., Wu, Z., Zhou, S., & Liu, S. (2017) · Renewable and Sustainable Energy Reviews · doi:10.1016/j.rser.2017.02.042 · Cited by 445
Discovery, Engineering, and Synthetic Application of Transaminase Biocatalysts
Slabu, I., Galman, J. L., Lloyd, R. C., & Turner, N. J. (2017) · ACS Catalysis · doi:10.1021/acscatal.7b02686 · Cited by 375
Self-citationEnantioselective Chemo‐ and Biocatalysis: Partners in Retrosynthesis
Hönig, M., Sondermann, P., Turner, N. J., & Carreira, E. M. (2017) · Angewandte Chemie International Edition · doi:10.1002/anie.201612462 · Cited by 284
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Metadata
- Authors
- O'Reilly, E., Iglesias, C., Ghislieri, D., Hopwood, J., Galman, J. L., Lloyd, R. C., & Turner, N. J.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2014-01-29
- Volume
- 53
- Issue
- 9
- Pages
- 2447-2450
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2161278159
- Cited by
- 182
- References
- 1
- FWCI
- 9.00
- Type
- journal article
- Language
- en
- Open access
- bronze
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- O'Reilly, E., Iglesias, C., Ghislieri, D., Hopwood, J., Galman, J. L., Lloyd, R. C., & Turner, N. J. (2014). A Regio‐ and Stereoselective ω‐Transaminase/Monoamine Oxidase Cascade for the Synthesis of Chiral 2,5‐Disubstituted Pyrrolidines. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.201309208
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