Jeremy I. Ramsden
Bifunctional Imine Reductase Cascades for the Synthesis of Saturated N-Heterocycles
Ramsden, Jeremy I.; Zucoloto da Costa, Bruna; Heath, Rachel S.; Marshall, James R.; Derrington, Sasha R.; Mangas-Sanchez, Juan; Montgomery, Sarah L.; Mulholland, Keith R.; Cosgrove, Sebastian C.; Turner, Nicholas J.
Authors
Bruna Zucoloto da Costa
Rachel S. Heath
James R. Marshall
Sasha R. Derrington
Juan Mangas-Sanchez
Sarah L. Montgomery
Keith R. Mulholland
Sebastian Cosgrove s.cosgrove@keele.ac.uk
Nicholas J. Turner
Abstract
Saturated N-heterocycles constitute a vital scaffold for pharmaceutical chemistry but are challenging to access synthetically, particularly asymmetrically. Here, we demonstrate how imine reductases can achieve annulation through tandem inter- and intramolecular reductive amination processes. Imine reductases were used in combination with further enzymes to access unsubstituted, α-substituted, and α,α′-disubstituted N-heterocycles from simple starting materials in one pot and under benign conditions. This work shows the remarkable flexibility of these enzymes to have broad activity against numerous substrates derived from singlular starting materials.
Citation
Ramsden, J. I., Zucoloto da Costa, B., Heath, R. S., Marshall, J. R., Derrington, S. R., Mangas-Sanchez, J., …Turner, N. J. (2024). Bifunctional Imine Reductase Cascades for the Synthesis of Saturated N-Heterocycles. ACS catalysis, 14(19), 14703-14710. https://doi.org/10.1021/acscatal.4c03832
Journal Article Type | Article |
---|---|
Acceptance Date | Sep 13, 2024 |
Online Publication Date | Sep 19, 2024 |
Publication Date | Oct 4, 2024 |
Deposit Date | Oct 4, 2024 |
Journal | ACS Catalysis |
Electronic ISSN | 2155-5435 |
Publisher | American Chemical Society |
Peer Reviewed | Peer Reviewed |
Volume | 14 |
Issue | 19 |
Pages | 14703-14710 |
DOI | https://doi.org/10.1021/acscatal.4c03832 |
Keywords | imine reductase; reductive aminase; cyclization; N-heterocycles |
Public URL | https://keele-repository.worktribe.com/output/948161 |
Publisher URL | https://pubs.acs.org/doi/10.1021/acscatal.4c03832 |
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