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Tailored Enzymatic Synthesis of Chitooligosaccharides with Different Deacetylation Degrees and Their Anti-Inflammatory Activity

1
Instituto de Catálisis y Petroleoquímica, CSIC, 28049 Madrid, Spain
2
Applied Biotechnology Group, Faculty of Biomedical and Health Sciences, Universidad Europea de Madrid, Villaviciosa de Odón, 28670 Madrid, Spain
3
Centro de Biología Molecular Severo Ochoa, CSIC-UAM, 28049 Madrid, Spain
*
Author to whom correspondence should be addressed.
Catalysts 2019, 9(5), 405; https://doi.org/10.3390/catal9050405
Received: 5 April 2019 / Revised: 24 April 2019 / Accepted: 28 April 2019 / Published: 30 April 2019
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Abstract

By controlled hydrolysis of chitosan or chitin with different enzymes, three types of chitooligosaccharides (COS) with MW between 0.2 and 1.2 kDa were obtained: fully deacetylated (fdCOS), partially acetylated (paCOS), and fully acetylated (faCOS). The chemical composition of the samples was analyzed by high-performance anion exchange chromatography with pulsed amperometric detection (HPAEC-PAD) and MALDI-TOF mass spectrometry. The synthesized fdCOS was basically formed by GlcN, (GlcN)2, (GlcN)3, and (GlcN)4. On the contrary, faCOS contained mostly GlcNAc, (GlcNAc)2 and (GlcNAc)3, while paCOS corresponded to a mixture of at least 11 oligosaccharides with different proportions of GlcNAc and GlcN. The anti-inflammatory activity of the three COS mixtures was studied by measuring their ability to reduce the level of TNF-α (tumor necrosis factor) in murine macrophages (RAW 264.7) after stimulation with a mixture of lipopolysaccharides (LPS). Only fdCOS and faCOS were able to significantly reduce the production of tumor necrosis factor (TNF)-α at 6 h after stimulation with lipopolysaccharides. View Full-Text
Keywords: biocatalysis; glycosidases; chitinases; chitosanases; chitosan oligosaccharides; deacetylation degree; anti-inflammatory biocatalysis; glycosidases; chitinases; chitosanases; chitosan oligosaccharides; deacetylation degree; anti-inflammatory
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Santos-Moriano, P.; Kidibule, P.; Míguez, N.; Fernández-Arrojo, L.; Ballesteros, A.; Fernández-Lobato, M.; Plou, F. Tailored Enzymatic Synthesis of Chitooligosaccharides with Different Deacetylation Degrees and Their Anti-Inflammatory Activity. Catalysts 2019, 9, 405.

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