Switchable product selectivity in dehydration of N-acetyl-d-glucosamine promoted by choline chloride-based deep eutectic solvents
Jiancheng Zhao, Christian Pedersen, Honghong Chang, Xianglin Hou, Yingxiong Wang, Yan Qiao
Abstract
Herein, we report choline chloride-based deep eutectic solvents (DESs) promoted conversion of N -acetyl-d-glucosamine (GlcNAc) into nitrogen-containing compounds, i.e., 3-acetamido-5-(1′,2′-dihydroxyethyl) furan (Chromogen III) and 3-acetamido-5-acetylfuran (3A5AF). The binary deep eutectic solvent choline chloride-glycerin (ChCl-Gly), was found to promote the dehydration of GlcNAc to form Chromogen III, which reaches a maximum yield of 31.1%. On the other hand, the ternary deep eutectic solvent, choline chloride-glycerol-B(OH) 3 (ChCl-Gly-B(OH) 3 ), promoted the further dehydration of GlcNAc into 3A5AF with a maximum yield of 39.2%. In addition, the reaction intermediate, 2-acetamido-2,3-dideoxy-d- erythro -hex-2-enofuranose (Chromogen I), was detected by in situ nuclear magnetic resonance (NMR) techniques when promoted by ChCl-Gly-B(OH) 3 . The experimental results of the 1 H NMR chemical shift titration showed ChCl-Gly interactions with α-OH-3 and α-OH-4 of GlcNAc, which is responsible for promoting the dehydration reaction. Meanwhile, the strong interaction between Cl − and GlcNAc was demonstrated by 35 Cl NMR.