title: Mimetics of the tri- and tetrasaccharide epitope of GQ1balpha as myelin-associated glycoprotein (MAG) ligands.
abstract: The synthesis of phenoxyphenyl, phenoxybenzyl, biphenyl, and phenyltriazole substituted sialic acid derivatives as mimics of the tri- and tetrasaccharide epitopes of GQ1balpha is described. These synthetically easily available sialosides show comparable or even enhanced affinity to MAG compared with the natural tri- and tetrasaccharide epitopes and form a new class of potential MAG antagonists.
authors.affiliation: Institute of Molecular Pharmacy, Pharmacenter, University of Basel, Klingelbergstrasse 50, CH-4056 Basel, Switzerland.
authors.forename: Ganpan
authors.initials: G
authors.lastname: Gao
authors.forename: Martin
authors.initials: M
authors.lastname: Smiesko
authors.forename: Oliver
authors.initials: O
authors.lastname: Schwardt
authors.forename: Heiko
authors.initials: H
authors.lastname: Gäthje
authors.forename: Soerge
authors.initials: S
authors.lastname: Kelm
authors.forename: Angelo
authors.initials: A
authors.lastname: Vedani
authors.forename: Beat
authors.initials: B
authors.lastname: Ernst
mesh_terms: D002240:Carbohydrate Sequence; D000939:Epitopes / Q000737:chemistry / Q000494:pharmacology*; D005732:Gangliosides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008024:Ligands; D008958:Models, Molecular; D008968:Molecular Conformation; D018716:Molecular Mimicry; D008969:Molecular Sequence Data; D018992:Myelin-Associated Glycoprotein / Q000737:chemistry / Q000187:drug effects*; D019158:N-Acetylneuraminic Acid / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011134:Polysaccharides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D014312:Trisaccharides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000939:Epitopes; D005732:Gangliosides; D008024:Ligands; D018992:Myelin-Associated Glycoprotein; D011134:Polysaccharides; D014312:Trisaccharides; C084317:GQ1balpha ganglioside; D019158:N-Acetylneuraminic Acid