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Direct conversion of shrimp shells to O-acylated chitin with antibacterial and anti-tumor effect by natural deep eutectic solvent

Abstract

To obtain O-acylated chitin from shrimp shells directly, the used solvent should hold multiple functions to remove calcium carbonate, protein, and acylate chitin. Herein, we use the acid natural deep eutectic solvents (NADESs) with ability of release H+ and various hydrogen bonding sites to achieve the above goal. The involved NADESs with three abilities of decalcification, deproteinization and acylation replaced the acid, alkali, catalysis, and acylation reagents in the conventional method. The experiment results revealed that the components of the NADESs, experiment temperature and time played key roles in the purity and degree of substitution (DS) of O-acylated chitin. Meanwhile, the ratio of shrimp shells to NADESs and a small amount of water had little effect on the preparation of O-acylation. With the optimal NADES (choline chloride/DL-malic acid 1:2, ChCl 1-DL Mal 2) treatment in the optimal conditions, the purity of O-malate chitin reached to 98.6 % with DS 0.46, exhibiting antibacterial and anti-tumor effect. The experiments results showed that the removal of calcium carbonate and protein, and acylation of chitin were carried out simultaneously. Mechanistic exploration by spectrum instruments and experiments confirmed that released H+ from ChCl 1-DL Mal 2 was the main reason to remove calcium carbonate and cause acylation reaction. The protein was degraded to amino acids because of ChCl 1-DL Mal 2 acidity and dissolved in the NADES due to hydrogen bonding formation with ChCl 1-DL Mal 2.

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Publication details

The article was received on 09 Aug 2018, accepted on 08 Oct 2018 and first published on 09 Oct 2018


Article type: Paper
DOI: 10.1039/C8GC02506A
Citation: Green Chem., 2018, Accepted Manuscript
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    Direct conversion of shrimp shells to O-acylated chitin with antibacterial and anti-tumor effect by natural deep eutectic solvent

    M. Feng, X. Lu, J. Zhang, Y. Li, C. Shi, L. Lu and S. Zhang, Green Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8GC02506A

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