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Direct Conversion of Hydrazones to Amines using Transaminases

Carter, EM; Subrizi, F; Ward, JM; Sheppard, TD; Hailes, HC; (2021) Direct Conversion of Hydrazones to Amines using Transaminases. ChemCatChem 10.1002/cctc.202101008. (In press). Green open access

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Abstract

Transaminase enzymes (TAms) have been widely used for the amination of aldehydes and ketones, often resulting in optically pure products. In this work, transaminases were directly reacted with hydrazones in a novel approach to form amine products. Several substrates were investigated, including those with furan and phenyl moieties. It was determined that the amine yields increased when an additional electrophile was added to the reaction mixture, suggesting that they can sequester the hydrazine released in the reaction. Pyridoxal 5’-phosphate (PLP), a cofactor for transaminases, and polyethylene glycol (PEG)-aldehydes were both found to increase the yield of amine formed. Notably, the amination of (S)-(−)-1-amino-2-(methoxymethyl)pyrrolidine (SAMP) hydrazones gave promising results as a method to form chiral β-substituted amines in good yield.

Type: Article
Title: Direct Conversion of Hydrazones to Amines using Transaminases
Open access status: An open access version is available from UCL Discovery
DOI: 10.1002/cctc.202101008
Publisher version: https://doi.org/10.1002/cctc.202101008
Language: English
Additional information: © 2021 The Authors. ChemCatChem published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/).
Keywords: amines, biocatalysis, enzymes, hydrazones, transaminases
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Engineering Science
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Engineering Science > Dept of Biochemical Engineering
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
URI: https://discovery.ucl.ac.uk/id/eprint/10134786
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