Mimetics of the tri- and tetrasaccharide epitope of GQ1balpha as myelin-associated glycoprotein (MAG) ligands.
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.
Gao
Ganpan
G
Institute of Molecular Pharmacy, Pharmacenter, University of Basel, Klingelbergstrasse 50, CH-4056 Basel, Switzerland.
Smiesko
Martin
M
Schwardt
Oliver
O
Gäthje
Heiko
H
Kelm
Soerge
S
Vedani
Angelo
A
Ernst
Beat
B
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*
D000939:Epitopes; D005732:Gangliosides; D008024:Ligands; D018992:Myelin-Associated Glycoprotein; D011134:Polysaccharides; D014312:Trisaccharides; C084317:GQ1balpha ganglioside; D019158:N-Acetylneuraminic Acid