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Stereoselective Transaminase-Mediated Synthesis of Serotonin and Melatonin Receptor Agonists

Baud, Damien; Tappertzhofen, Nadine; Moody, Thomas S; Ward, John M; Hailes, Helen C; (2022) Stereoselective Transaminase-Mediated Synthesis of Serotonin and Melatonin Receptor Agonists. Advanced Synthesis & Catalysis 10.1002/adsc.202200146. (In press). Green open access

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Abstract

Transaminase enzymes have significant potential for the stereoselective synthesis of drugs or drug precursors. Here, starting from one prochiral β-tetralone, a short and efficient chemoenzymatic synthesis of four agonists of the serotonin/melatonin receptors have been developed. The key step is the stereoselective transamination of the prochiral ketone to produce both enantiomers of 8-methoxy-2-aminotetraline in high yields and enantiomeric excesses. This was followed by either amidation to give the 8-methoxy-2-acetimidotetralines or several facile chemical steps to the 8-hydroxy-2-aminodipropyltetralines.

Type: Article
Title: Stereoselective Transaminase-Mediated Synthesis of Serotonin and Melatonin Receptor Agonists
Open access status: An open access version is available from UCL Discovery
DOI: 10.1002/adsc.202200146
Publisher version: https://doi.org/10.1002/adsc.202200146
Language: English
Additional information: © 2022 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Keywords: Biocatalysis; transaminases; aminotetralines; chemoenzymatic
UCL classification: UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL
URI: https://discovery.ucl.ac.uk/id/eprint/10147128
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