Syntheses of beta-D-GalpNAc4SO3-(1-->4)-L-IdopA2SO3, a disaccharide fragment of dermatan sulfate, and of its methyl alpha-L-glycoside derivative.
The syntheses of sodium (sodium 2-acetamido-2-deoxy-4-O-sulfonato-beta-D-galactopyranosyl)-(1-->4)-(sodium 2-O-sulfonato-L-idopyran)uronate, a disaccharide fragment of dermatan sulfate, and of its methyl alpha-L-glycoside derivative are reported for the first time. The use of 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl-alpha-D-galactopyranose, readily prepared from a D-gluco precursor, allowed the stereocontrolled and high yielding coupling with the low reactive 4-hydroxyl group of L-iduronic acid ester derivatives. Classical transformation of the disaccharide products into the target molecules was achieved in high yield.
Barroca
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Institut de Chimie Organique et Analytique, UPRES-A CNRS 6005, UFR Faculté des Sciences, Université d'Orléans, France.
Jacquinet
J C
JC
D003871:Dermatan Sulfate / Q000737:chemistry*; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D004187:Disaccharides; C421203:GalpNAc4So3-(1-4)-IdopA2SO3; D003871:Dermatan Sulfate