Syntheses and Properties of Novel Vinyl Monomers Bearing a Glycoside Residue

Abstract

Novel acrylic monomers bearing a monosaccharide residue were synthesized in reactions of some methyl glycosides with 2-hydroxylethyl acrylate or methacrylate in the presence of heteropoly acid. All of them were highly soluble in water and readily polymerized by radical initiators.

Kinetic study on the binding of lectin to mannose residues in a polymer brush

“…The abbreviation "DT" was used for disulfide group-carrying (dithiolated) compounds hereafter. 2-Methacryloyloxyethyl Dmannopyranoside (MEMan, a mixture of ␣-and ␤-anomers (7.3:2.7)) was prepared from 2-hydroxyethyl methacrylate (HEMA) and methyl ␣-D-mannopyranside (␣-MeMan) using a heteropolyacid as catalyst as reported previously [49]. Methacrylic acid (MA) from Wako Pure Chemicals, Osaka, Japan, and N,N-dimethyl acrylamide (DMAA) from Kohjin, Tokyo, Japan, were distilled at low pressure.…”

Synthesis and characterization of water-soluble glucosyloxyethyl acrylate modified chitosan

“…Glucosyloxyethyl acrylate (GEA) was synthesized from the transesterification of ␣-d-glucopyranoside and HEA by using phosphomolybdic acid as a catalyzer according to Ref. [19]. Other reagents were all obtained from Beijing Chemical Agent Co. (Beijing, China) and used as received.…”

“…GEA is a kind of acrylic monomers bearing a monosaccharide residue [19], and polymers bearing saccharide residues on their side chain have unique properties to be used as pharmacological or biomedical materials and play important roles in the intercellular recognition process [20]. The glucosyloxyethyl acrylation of chitosan here would not only improve the water-solubility of chitosan, but also introduce stronger specific interactions with lectins as concanavalin A, thus would be helpful to develop glucose-sensitive systems, which would be investigated in our further research.…”

Glucose and pH dual-responsive concanavalin A based microhydrogels for insulin delivery

“…Glucosyloxyethyl methacrylate (GEMA), a kind of acrylic monomer bearing a monosaccharide residue was synthesized by the reaction of methyl glycoside with an excess amount of 2-hydroxyethyl methacrylate (2-HEMA) in the presence of heteropoly acid catalyst and polymerization inhibitor [24]. Briefly, methyl ␣-d-glucopyranoside (9.7 g, 0.05 mol) was suspended in a mixture of HEMA (65 g, 0.5 mol) and chlorobenzene (13 g) containing phosphomolybdic acid (1 g) as a catalyst and p-hydroxyanisole (1 g) as an inhibitor.…”