Synthesis of 2-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-D-mannose, and its interaction with D-mannose-specific lectins.
Condensation of 3, 4:5, 6-di-O-isopropylidene-D-mannose dimethyl acetal with 2-methyl-(3, 4, 6-tri-O-acetyl-1, 2-dideoxy-alpha-D-glucopyrano)-[2', 1':4, 5]-2- oxazoline in the presence of a catalytic amount of p-toluenesulfonic acid afforded crystalline 2-O-(2-acetamido-3, 4, 6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-3, 4:5, 6-di-O-isopropylidene-D-mannose dimethyl acetal (3) in 25 percent yield. Catalytic deacetylation of 3 with sodium methoxide, followed by hydrolysis with dilute sulfuric acid, gave 2-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-D-mannose (4). Treatment of 3 with boiling 0.5 percent methanolic hydrogen chloride under reflux gave methyl 2-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-alpha-D-mannopyranoside (5) and methyl 2-o-2-acetamido-2-deoxy-beta-D-glucopyranosyl)-alpha-D-mannofuranoside (6). The inhibitoryactivities of 4, 5, and 6 against the hemagglutinating and mitogenic activities of Lens culinaris and Pisum sativum lectins and concanavalin A were assayed. From the results of these hapten inhibition studies, subtle differences of specificity between these D-mannose-specific lectins were confirmed.
D001665:Binding Sites; D003208:Concanavalin A; D004247:DNA / Q000096:biosynthesis; D004187:Disaccharides / Q000138:chemical synthesis / Q000494:pharmacology; D005944:Glucosamine / Q000494:pharmacology; D006385:Hemagglutination Inhibition Tests; D006801:Humans; D037102:Lectins; D008214:Lymphocytes / Q000187:drug effects / Q000378:metabolism; D008358:Mannose / Q000494:pharmacology; D009904:Optical Rotation; D013055:Spectrophotometry, Infrared; D013936:Thymidine / Q000378:metabolism
D004187:Disaccharides; D037102:Lectins; D003208:Concanavalin A; D004247:DNA; D005944:Glucosamine; D008358:Mannose; D013936:Thymidine