O-Sulfated Derivatives of Glucuronic Acid
نویسندگان
چکیده
4-O-Substituted D-glucuronic acid derivatives were synthesized from D-glucose in order to study the regioselectivity of sulfation. Introduction Glycosaminoglycans, as heparin and heparan sulfate, interact with various proteins, and their binding properties are related to the glycosidic sequence and the number and position of sulfate groups. In our laboratory, we performed a variety of chemical modifications of the polysaccharide chain. On sulfation of heparan sulfate, the regioselective sulfation of glucuronic acid units in O-2 has been observed. This result is interesting due to biological properties of heparan sulfate. Experimental The synthesis of derivatives of glucuronic acid was performed as shown in Fig. 1. Figure 1. O OMe OH HO HO OH O OMe OBn BnO O O Ph O OMe OBn BnO HO OH O OMe OBn BnO MeO COOBn O OMe OH HO MeO COO-Na+ O OMe OBn BnO MeO OTBS 1 2 3
منابع مشابه
Investigations on the Chemistry of Heparin
The position of the O-sulfates in heparin was investigated by methylation procedures. Heparin was converted to the acetamido derivative and permethylated with diiethyl sulfate in aqueous alkali. Other methylation methods in organic solvents were also used. The carboxyl groups in the uranic acid moieties were then reduced and the resulting permethylated polysaccharide was hydrolyzed. The product...
متن کاملSynthesis of 4-(trifluoromethyl) coumarins using nano sulfated-titania as solid acid catalyst under solvent-free conditions
Nano sulfated titania was tested as solid acid heterogeneous catalyst for the synthesis of 4-(Trifluoromethyl) coumarin and coumarin derivatives under solvent-free condition. Factorial design evidenced a positive effect of reaction temperature, amount of catalyst, and solvents. This nano-sized sulfated titania has been prepared by a sol-gel hydrothermal process. The prepared sulfated titania s...
متن کاملOccurrence of a unique fucose-branched chondroitin sulfate in the body wall of a sea cucumber.
The sulfated polysaccharides in the body wall of the sea cucumber occur as three fractions that differ markedly in molecular mass and chemical composition. The fraction containing a high molecular mass component has a high proportion of fucose and small amounts of galactose and amino sugars, whereas another fraction contains primarily a sulfated fucan. The third fraction (F-2), which represents...
متن کاملSynthesis of 4-(trifluoromethyl) coumarins using nano sulfated-titania as solid acid catalyst under solvent-free conditions
Nano sulfated titania was tested as solid acid heterogeneous catalyst for the synthesis of 4-(Trifluoromethyl) coumarin and coumarin derivatives under solvent-free condition. Factorial design evidenced a positive effect of reaction temperature, amount of catalyst, and solvents. This nano-sized sulfated titania has been prepared by a sol-gel hydrothermal process. The prepared sulfated titania s...
متن کاملStructural studies on sulfated oligosaccharides derived from the carbohydrate-protein linkage region of chondroitin sulfate proteoglycans of whale cartilage.
From the carbohydrate-protein linkage region of whale cartilage proteoglycans, which bear predominantly chondroitin 4-sulfate, one nonsulfated, two monosulfated and one disulfated hexasaccharide alditols were isolated after exhaustive digestions with Actinase E and chondroitinase ABC, and subsequent beta-elimination. Their structures were analyzed by chondroitinase ACII digestion in conjunction...
متن کامل