Method for producing synthetic N-linked glycoconjugates
AssigneeMonsanto Company
InventorsThomas W. Rademacher, Ian D. Manger, Simon Wong, Raymond A. Dwek
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Abstract
A method is disclosed for derivatizing oligosaccharides to form synthetic N-linked glycoconjugates by converting a glycosylamine derivative of the oligosaccharide to a haloacetylated derivative as an intermediate compound prior to formation of the synthetic N-linked glycoconjugate to thereby directly maintain the .beta.-anomeric configuration of said N-linked glycoconjugate.
Claims21
A process for producing synthetic N-linked glycoconjugates of oligosaccharides under conditions to directly maintain the closed ring structure of the terminal monosaccharide of said oligosaccharides in the .beta.-anomeric configuration comprising reacting an oligosaccharide in saturated ammonium bicarbonate at pH of from about 8 to about 8.5 to form a .beta.-glycosylamine derivative of said oligosaccharide, haloacetylating said .beta.-glycosamine derivative in aqueous phase reaction to directly form the 1-N-haloacetamido derivative of said .beta.-glycosamine derivative without selective crystallization in organic solvent medium, converting said 1-N-haloacetamido derivative to a 1-N-glycyl-.beta.-glycosylamine intermediate derivative by ammonolysis and thereafter reacting said 1-N-glycyl-.beta.-glycosylamine intermediate derivative with a substrate capable of forming a 1-N-glycyl-.beta.-glycosylamine linked glycoconjugate of said substrate and said 1-N-glycyl-.beta.-glycosylamine derivative.
A process for producing a synthetic N-linked glycoconjugate of an oligosaccharide and a peptide under conditions to directly maintain the closed ring structure of the terminal monocaccharide of said oligosaccharide in .beta.-anomeric configuration without need for selective crystallization in organic solvent medium comprising reacting an oligosaccharide in saturated ammonium bicarbonate at pH of from about 8 to about 8.5 to form a .beta.-glycosylamine derivative of said oligosaccharide and thereafter reacting said .beta.-glycosylamine derivative with a peptide having an activated carboxyl group capable of forming a .beta.-glycosylamine linked glycoconjugate of said peptide and said .beta.-glycosylamine derivative.
Dependencies are inferred from the claim text.