1. Synthetic assembly of α-O-linked-type GlcNAc using polymer chemistry affords sugar clusters, which effectively bind to lectins.
- Author
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Nakada, Jyuichi, Matsushita, Takahiko, Koyama, Tetsuo, Hatano, Ken, and Matsuoka, Koji
- Subjects
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POLYMERS , *FLUORIMETRY , *WHEAT germ , *CARBOHYDRATES , *RADICALS (Chemistry) , *CROSSLINKED polymers , *LECTINS , *SNAKE venom , *ALIPHATIC alcohols - Abstract
[Display omitted] • Fischer's glycoside synthesis effectively worked with alcohols with longer aliphatic chains. • Glycopolymers having α-glycoside-type GlcNAc moieties were prepared. • Sugar densities on the glycopolymers were controlled. • Biological evaluations of glycopolymers—WGA were tested. • Glycopolymer having an appropriate sugar-density showed the highest affinity. Fischer's glycoside synthesis was applied to linker precursor alcohols of two different lengths having appropriate alkane chains to obtain the corresponding α-glycoside and it was found to be applicable with moderate yields. Water-soluble glycomonomers were systematically prepared from N -acetyl- d -glucosamine (GlcNAc) by introducing two kinds of alcohols having different methylene lengths. Typical radical polymerizations of the glycomonomers with acrylamide as a modulator for control of the distance between carbohydrate residues in water in the presence of ammonium persulfate (APS)- N , N , N' , N' -tetramethylethylenediamine (TEMED) gave a series of glycopolymers with various α-glycoside-type GlcNAc residue densities. Fluorometric analysis of the interaction of wheat germ agglutinin (WGA) with the glycopolymers was performed and the results showed unique binding specificities based on structural differences. [ABSTRACT FROM AUTHOR]
- Published
- 2024
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