title: Strong aphicidal activity of GlcNAc(β1→4)Glc disaccharides: synthesis, physiological effects, and chitinase inhibition.
abstract: The synthesis of four GlcNAc(β1→4)Glc disaccharides containing 2-O-acetyl and/or 6-sulfate groups was performed in high yields with total 1,2-trans stereoselectivity. These disaccharides were evaluated as candidates for insect chitinase inhibition and aphicidal activity. All the compounds prepared displayed physiological effects on M. persicae aphids; however, the inhibition of chitinases of different sources (bacteria, fungus, and aphid) followed different patterns according to subtle structural characteristics.
authors: Laboratoire des Glucides CNRS FRE 3517, Institut de Chimie de Picardie, Université de Picardie Jules Verne, 33 Rue Saint-Leu, 80039 Amiens Cedex 1, France.
authors: Christophe
authors: C
authors: Dussouy
authors: Laurent
authors: L
authors: Bultel
authors: Julien
authors: J
authors: Saguez
authors: Anas
authors: A
authors: Cherqui
authors: Mounia
authors: M
authors: Khelifa
authors: Eric
authors: E
authors: Grand
authors: Philippe
authors: P
authors: Giordanengo
authors: José
authors: J
authors: Kovensky
mesh_terms: D000818:Animals; D001042:Aphids / Q000737:chemistry* / Q000187:drug effects* / Q000378:metabolism; D002688:Chitinases / Q000037:antagonists & inhibitors* / Q000737:chemistry* / Q000494:pharmacology; D002849:Chromatography, Gas; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology*; D006031:Glycosylation; D007313:Insecta / Q000737:chemistry* / Q000187:drug effects* / Q000378:metabolism; D008320:Maltose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C097320:2-acetamido-2-deoxy-4-O-(beta-2-acetamid-2-deoxyglucopyranosyl)glucopyranose; D004187:Disaccharides; D008320:Maltose; D002688:Chitinases