Journal
CARBOHYDRATE RESEARCH
Volume 460, Issue -, Pages 8-13Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2018.01.010
Keywords
Chondroitin sulfate; Regioselective desulfation; Structural characterization
Funding
- NSFC-Shandong Joint Fund [U1606403]
- Innovation Project of Qingdao National Laboratory for Marine Science and Technology [2015ASKJ02]
- Shandong key scientific and technology program [2015ZDJS04002]
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The sulfation pattern plays a crucial role in chondroitin sulfate (CS) biological activity, and preparation of CS with defined structure is essential for accurate pharmacological study. In this study, we focused on the preparation of regioselective 4-O/6-O-desulfated CS derived from porcine, employing a dimethyl sulfoxide-methanol (DMSO-MeOH) method and an N-methyl-N-(trimethylsilyl) -trifluoroacetamide (MTSTFA) method CS, respectively. Results showed that the sulfate at C4 position (4-O-S) of N-acetyl-galactosamine (GalNAc) was selectively removed by the DMSO-MeOH method, and the sulfate at C6 position (6-O-S) of GalNAc was selectively removed by the MTSTFA method. Structures of desulfated CS were characterized by means of FT-IR, NMR and disaccharide composition analysis. The preparations of regioselective 4-O/6-O-desulfated CS are powerful for the study of structure-activity relationship of CS. (C) 2018 Elsevier Ltd. All rights reserved.
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