In the present study, regioselective sulfation of β-glucan (GLP) from Ganoderma lucidum were firstly established by using 4,4'-dimethoxytrityl chloride and hexamethyldisilazane as protecting precursor. 2,4,6-O-sulfated, 6-O-sulfated and 2,4-O-sulfated GLP derivatives were prepared and the molecular weights (M) of derivatives were determined to range from 0.94 × 10 to 6.27 × 10 g/mol, while the degrees of sulfation (DS) were calculated to vary from 0.83 to 1.74. The regioselective sulfation of GLP was confirmed by FT-IR, C NMR spectroscopy and methylation analysis. Results indicated that the sulfated substitution sites were predominantly at C-6 in 6-O-sulfated GLP (SGLP) and C-4 in 2,4-O-sulfated GLP (SGLP), respectively. Clotting assays (APTT, PT and TT) in vitro showed that sulfate groups were essential for anticoagulant activity and SGLP exhibited much higher than others. Meanwhile, sulfated GLP with higher DS and M showed stronger anticoagulant activity in the case of the same condition.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.ijbiomac.2020.03.234 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Visible-light-induced synthesis of bibenzofuranones a cerium-mediated energy transfer process.
Chem Commun (Camb)
March 2025
The State Key Laboratory of Applied Organic Chemistry, and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
Benzofuran-3(2)-one compounds are important bioactive molecules. Synthesis of bibenzofuranones from benzils a radical cyclization-dimerization tandem process, efficiently constructing the C-O/C-C bonds and contiguous quaternary carbon centers in a single step was reported. This reaction exhibits high regioselectivity, affording bibenzofuranones in moderate to excellent yields under mild conditions.
View Article and Find Full Text PDFMultifunctions of Sustainable Chondroitin Sulfates with Predominant Subtypes and Low Molecular Weights on Neurite Outgrowth.
Biomacromolecules
February 2025
School of Life Science and Health Engineering, Jiangnan University, Wuxi 214122, China.
Three chondroitin sulfate (CS) analogues with predominant subtypes (A, C, and E) were prepared from engineered K4 combined with regioselective sulfation. CS with the designed sulfates as the main components was characterized by nuclear magnetic resonance spectroscopy, elementary analysis, and disaccharide analysis. CS prepared from the native or degraded capsular polysaccharide had molecular weights of 1.
View Article and Find Full Text PDFRegioselective sulfation of alginate at 2-O-position of mannuronic acid unit with Py∙SO in DMSO.
Carbohydr Res
November 2024
Institute of Natural Sciences and Health, Tallinn University, Narva mnt 29, 10120, Tallinn, Estonia.
Alginates are brown algal polysaccharides consisting of β-D-mannuronic (M) and α-l-guluronic acid (G) residues linked with 1→4 glycosidic bonds. To functionalize these natural resources for biomedical use, alginates can be chemically modified, including by sulfation. Here regioselective sulfation of alginates at M-2 in DMSO with Py∙SO is described, by either sulfating alginates directly or through using alginates with added protecting groups (PG-s), including TBDMS-ether, Piv-, Bz-esters and intramolecular 3,6-lactone.
View Article and Find Full Text PDFStructural relationship of regioselectively-sulfonated botryosphaeran derivatives on activity against herpes simplex virus type 1.
Int J Biol Macromol
August 2024
Departamento de Química, CCE, Universidade Estadual de Londrina, Londrina, Paraná, Brazil. Electronic address:
Article Synopsis
- The study investigates the antiviral activities of sulfonated polysaccharides, specifically focusing on the exocellular fungal glucan botryosphaeran and its regioselective sulfonation methods: mild sulfonation (MS) and pivaloyl ester (PS).
- Two derivatives were created with different substitution patterns, showing varying degrees of sulfonation and specificities at C-6 for MS and C-2/C-4 for PS.
- The MS derivative exhibited strong antiviral effects against Herpes simplex virus type 1 (HSV-1), while PS showed no activity, highlighting that sulfate groups at the C-6 position enhance antiviral properties.
A Biomimetic Synthetic Strategy Can Provide Keratan Sulfate I and II Oligosaccharides with Diverse Fucosylation and Sulfation Patterns.
J Am Chem Soc
April 2024
Department of Chemical Biology and Drug Discovery, Utrecht Institute for Pharmaceutical Sciences, and Bijvoet Center for Biomolecular Research, Utrecht University, Universiteitsweg 99, 3584 CG Utrecht, The Netherlands.
Keratan sulfate (KS) is a proteoglycan that is widely expressed in the extracellular matrix of various tissue types, where it performs multiple biological functions. KS is the least understood proteoglycan, which in part is due to a lack of panels of well-defined KS oligosaccharides that are needed for structure-binding studies, as analytical standards, to examine substrate specificities of keratinases, and for drug development. Here, we report a biomimetic approach that makes it possible to install, in a regioselective manner, sulfates and fucosides on oligo--acetyllactosamine (LacNAc) chains to provide any structural element of KS by using specific enzyme modules.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!