Aminopolyols from Carbohydrates: Amination of Sugars and Sugar-Derived Tetrahydrofurans with Transaminases.

Fabiana Subrizi, Laure Benhamou, John M Ward, Tom D Sheppard, Helen C Hailes

Angewandte Chemie (International ed. in English) 2019 Mar 18

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Carbohydrates are the major component of biomass and have unique potential as a sustainable source of building blocks for chemicals, materials, and biofuels because of 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. Demonstrated here is 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. © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Citation

Fabiana Subrizi, Laure Benhamou, John M Ward, Tom D Sheppard, Helen C Hailes. Aminopolyols from Carbohydrates: Amination of Sugars and Sugar-Derived Tetrahydrofurans with Transaminases. Angewandte Chemie (International ed. in English). 2019 Mar 18;58(12):3854-3858