Transaminase triggered aza-Michael approach for the enantioselective synthesis of piperidine scaffolds
The expanding “toolbox” of biocatalysts opens new opportunities to redesign synthetic strategies to target molecules by incorporating a key enzymatic step into the synthesis. Herein, we describe a general biocatalytic approach for the enantioselective preparation of 2,6-disubstituted piperidines sta...
| Main Authors: | , , , , , |
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| Format: | Article |
| Published: |
American Chemical Society
2016
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| Online Access: | https://eprints.nottingham.ac.uk/39699/ |
| _version_ | 1848795894376300544 |
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| author | Ryan, James Šiaučiulis, Mindaugas Gomm, Andrew Macia, Beatriz O'Reilly, Elaine Caprio, Vittorio |
| author_facet | Ryan, James Šiaučiulis, Mindaugas Gomm, Andrew Macia, Beatriz O'Reilly, Elaine Caprio, Vittorio |
| author_sort | Ryan, James |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | The expanding “toolbox” of biocatalysts opens new opportunities to redesign synthetic strategies to target molecules by incorporating a key enzymatic step into the synthesis. Herein, we describe a general biocatalytic approach for the enantioselective preparation of 2,6-disubstituted piperidines starting from easily accessible pro-chiral ketoenones. The strategy represents a new biocatalytic disconnection, which relies on an ω-TA-mediated aza-Michael reaction. Significantly, we show that the reversible enzymatic process can power the shuttling of amine functionality across a molecular framework, providing access to the desired aza-Michael products. |
| first_indexed | 2025-11-14T19:39:20Z |
| format | Article |
| id | nottingham-39699 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T19:39:20Z |
| publishDate | 2016 |
| publisher | American Chemical Society |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-396992020-05-04T18:21:44Z https://eprints.nottingham.ac.uk/39699/ Transaminase triggered aza-Michael approach for the enantioselective synthesis of piperidine scaffolds Ryan, James Šiaučiulis, Mindaugas Gomm, Andrew Macia, Beatriz O'Reilly, Elaine Caprio, Vittorio The expanding “toolbox” of biocatalysts opens new opportunities to redesign synthetic strategies to target molecules by incorporating a key enzymatic step into the synthesis. Herein, we describe a general biocatalytic approach for the enantioselective preparation of 2,6-disubstituted piperidines starting from easily accessible pro-chiral ketoenones. The strategy represents a new biocatalytic disconnection, which relies on an ω-TA-mediated aza-Michael reaction. Significantly, we show that the reversible enzymatic process can power the shuttling of amine functionality across a molecular framework, providing access to the desired aza-Michael products. American Chemical Society 2016-11-10 Article PeerReviewed Ryan, James, Šiaučiulis, Mindaugas, Gomm, Andrew, Macia, Beatriz, O'Reilly, Elaine and Caprio, Vittorio (2016) Transaminase triggered aza-Michael approach for the enantioselective synthesis of piperidine scaffolds. Journal of the American Chemical Society, 138 (49). pp. 15798-15800. ISSN 1520-5126 http://pubs.acs.org/doi/abs/10.1021/jacs.6b07024 doI:10.1021/jacs.6b07024 doI:10.1021/jacs.6b07024 |
| spellingShingle | Ryan, James Šiaučiulis, Mindaugas Gomm, Andrew Macia, Beatriz O'Reilly, Elaine Caprio, Vittorio Transaminase triggered aza-Michael approach for the enantioselective synthesis of piperidine scaffolds |
| title | Transaminase triggered aza-Michael approach for the enantioselective synthesis of piperidine scaffolds |
| title_full | Transaminase triggered aza-Michael approach for the enantioselective synthesis of piperidine scaffolds |
| title_fullStr | Transaminase triggered aza-Michael approach for the enantioselective synthesis of piperidine scaffolds |
| title_full_unstemmed | Transaminase triggered aza-Michael approach for the enantioselective synthesis of piperidine scaffolds |
| title_short | Transaminase triggered aza-Michael approach for the enantioselective synthesis of piperidine scaffolds |
| title_sort | transaminase triggered aza-michael approach for the enantioselective synthesis of piperidine scaffolds |
| url | https://eprints.nottingham.ac.uk/39699/ https://eprints.nottingham.ac.uk/39699/ https://eprints.nottingham.ac.uk/39699/ |