Switchable product selectivity in dehydration of N-acetyl-D-glucosamine promoted by choline chloride-based deep eutectic solvents
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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.
Original language | English |
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Article number | 106980 |
Journal | iScience |
Volume | 26 |
Issue number | 7 |
Number of pages | 12 |
ISSN | 2589-0042 |
DOIs | |
Publication status | Published - 21 Jul 2023 |
Bibliographical note
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)
- Green chemistry, Organic chemistry
Research areas
ID: 366816549