Hailes, HC;
Subrizi, F;
Benhamou, L;
Ward, J;
Sheppard, T;
(2019)
Aminopolyols from carbohydrates: the amination of sugars and sugar‐derived tetrahydrofurans with transaminases.
Angewandte Chemie International Edition
, 58
(12)
pp. 3854-3858.
10.1002/anie.201813712.
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Benhamou Aminopolyols from Carbohydrates Aminationof Sugars and Sugar-Derived Tetrahydrofurans withTransaminases.pdf - Published Version Download (2MB) | Preview |
Abstract
Carbohydrates are the major component of biomass and have unique potential as a sustainable source of building blocks for chemicals, materials and biofuels due to their low cost, ready availability and stereochemical diversity. With a view to upgrading carbohydrates to access valuable nitrogen containing sugar-like compounds such as aminopolyols, biocatalytic aminations using transaminase enzymes (TAms) have been investigated as a sustainable alternative to traditional synthetic strategies. Here we demonstrate the reaction of TAms with sugar-derived tetrahydrofuran (THF) aldehydes, obtained from the regioselective dehydration of biomass-derived sugars, to provide access to cyclic aminodiols in high yields. In a preliminary study we have also established the direct transamination of sugars to give acyclic aminopolyols. Notably, the reaction of the ketose D-fructose proceeds with complete stereoselectivity to yield valuable aminosugars in high purity.
| Type: | Article |
|---|---|
| Title: | Aminopolyols from carbohydrates: the amination of sugars and sugar‐derived tetrahydrofurans with transaminases |
| Location: | Germany |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1002/anie.201813712 |
| Publisher version: | https://doi.org/10.1002/anie.201813712 |
| Language: | English |
| Additional information: | Copyright © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. 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, aminopolyols, biomass waste, sugars, 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/10067131 |
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