New strategy in glycopolymer synthesis. Preparation of antigenic water-soluble poly(acrylamide-co-p-acrylamidophenyl beta-lactoside).
Stereospecific phase-transfer-catalyzed glycosidation of acetobromolactose 3 with p-nitrophenoxide gave the peracetylated 1,2-trans-beta-D-4-nitrophenyl lactoside 4. Functionalization of 4 into an N-acryloyl monomer was achieved by catalytic transfer hydrogenation of the nitro group, followed by N-acryloylation of the resulting amino group, on both O-acetyl-protected and unprotected disaccharides. Copolymerization of 4-acrylamidophenyl beta-lactoside (9) with acrylamide, initiated by ammonium persulfate, afforded a water-soluble carbohydrate copolymer (glycopolymer). The antigenicity of the new polymer was demonstrated by agar gel diffusion with Arachis hypogaea (peanut) and Ricinus communis (castor bean) lectins. Quantitative precipitation and enzyme linked lectin assays (ELLA) were also performed with peanut lectin.
Roy
R
R
Department of Chemistry, University of Ottawa, Ontario, Canada.
Tropper
F D
FD
Romanowska
A
A
D000180:Acrylic Resins / Q000138:chemical synthesis*; D000941:Antigens / Q000032:analysis*; D010367:Arachis; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006027:Glycosides / Q000138:chemical synthesis*; D006735:Horseradish Peroxidase; D007202:Indicators and Reagents; D037102:Lectins; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009904:Optical Rotation; D019887:Peanut Agglutinin; D037121:Plant Lectins; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D012276:Ricin
D000180:Acrylic Resins; D000941:Antigens; D006027:Glycosides; D007202:Indicators and Reagents; D037102:Lectins; D019887:Peanut Agglutinin; D037121:Plant Lectins; D011134:Polysaccharides; C076594:poly(acrylamide-co-4-acrylamidophenyl lactoside); D012276:Ricin; D006735:Horseradish Peroxidase