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

摘要

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 stereo selectivity to yield valuable aminosugars in high purity.