Conversion of aldoses to valuable ω-amino alcohols using amine transaminase biocatalysts

Cairns, Ryan; Gomm, Andrew; Ryan, James; Clarke, Thomas; Kulcinskaja, Evelina; Butler, Kevin; O�Reilly, Elaine

Abstract

The conversion of readily available monosaccharides to high-value amino alcohols using a key biocatalytic step is an attractive strategy for the preparation of these chiral synthons. Here, we report a previously undescribed example of the direct amination of monosaccharides, which exist predominantly in their cyclic form at equilibrium, using amine transaminase biocatalysts, providing access to a panel of amino alcohols in moderate to high conversion and isolated yield. A recently developed high-throughput colorimetric screen, employing o-xylylenediamine, was initially used to identify amine transaminase enzymes displaying this activity towards cyclic sugars and reactions were successfully scaled-up using isopropylamine.

Citation

Cairns, R., Gomm, A., Ryan, J., Clarke, T., Kulcinskaja, E., Butler, K., & O’Reilly, E. (2019). Conversion of aldoses to valuable ω-amino alcohols using amine transaminase biocatalysts. ACS Catalysis, 9(2), 1220-1223. https://doi.org/10.1021/acscatal.8b04564

• Journal Article Type: Article
• Acceptance Date: Dec 28, 2018
• Online Publication Date: Dec 28, 2018
• Publication Date: Jan 15, 2019
• Deposit Date: Jan 28, 2019
• Publicly Available Date: Dec 29, 2019
• Journal: ACS Catalysis
• Electronic ISSN: 2155-5435
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 9
• Issue: 2
• Pages: 1220-1223
• DOI: https://doi.org/10.1021/acscatal.8b04564
• Public URL: https://nottingham-repository.worktribe.com/output/1500662
• Publisher URL: https://pubs.acs.org/doi/10.1021/acscatal.8b04564
• Contract Date: Jan 28, 2019