Subrizi, F; Benhamou, L; Ward, JM; Sheppard, TD; Hailes, HC; (2019) Aminopolyols from Carbohydrates: Amination of Sugars and Sugar‐Derived Tetrahydrofurans with Transaminases. Angewandte Chemie , 131 (12) pp. 3894-3898. 10.1002/ange.201813712.

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Abstract

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.

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