TY - JOUR

T1 - Switchable product selectivity in dehydration of N-acetyl-D-glucosamine promoted by choline chloride-based deep eutectic solvents

AU - Zhao, Jiancheng

AU - Pedersen, Christian Marcus

AU - Chang, Honghong

AU - Hou, Xianglin

AU - Wang, Yingxiong

AU - Qiao, Yan

N1 - Funding Information: The authors thank for National Natural Science Foundation of China ( 22075308 ) and Natural Science Foundation of Shanxi Province ( 202103021224439 ) for financial support. Publisher Copyright: © 2023 The Author(s)

PY - 2023/7/21

Y1 - 2023/7/21

N2 - 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 1H 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 35Cl NMR.

AB - 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 1H 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 35Cl NMR.

KW - Green chemistry

KW - Organic chemistry

U2 - 10.1016/j.isci.2023.106980

DO - 10.1016/j.isci.2023.106980

M3 - Journal article

C2 - 37332676

AN - SCOPUS:85161716973

VL - 26

JO - iScience

JF - iScience

SN - 2589-0042

IS - 7

M1 - 106980

ER -