Polymer-supported solution synthesis of oligosaccharides
First Claim
1. A process for the preparation of oligosaccharides which comprises:
- a) reacting a first reactant saccharide having at least one monosaccharide unit with a second reactant which is a polyethylene glycol monomethyl ether, the two reactants being linked through an ester linkage of dicarboxylic acid bound to a carbohydrate carboxyl;
b) subjecting the saccharide-polyethylene glycol monomethyl ether reaction product to a glycosylation reaction through a plurality of additions of a glycosylation agent having an activated anomeric center, while monitoring the reaction for completion;
c) isolating the polyethylene glycol-oligosaccharide as a solid;
d) purifying the solid; and
e) releasing the oligosaccharide from the polyethylene glycol.
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Abstract
This invention relates to the preparation of oligosaccharides, using polymer supported methodology. By this method, which offers anomeric control, oligosaccharides are produced very rapidly in comparison with known methodologies. Thus, there is disclosed a process for the preparation of oligosaccharides which comprises
a) forming a synthon of a saccharide and a monomethylether of polyethylene glycol or a derivative thereof, the synthon having a linkage between the oligosaccharide and the monomethylether of polyethylene glycol or a derivative thereof, which linkage can be severed under conditions that do not damage glycosidic or other bonds in a desired end product;
b) subjecting the synthon to repeated additions of a suitable glycosylating agent to form a desired oligosaccharide-polyethylene glycol linked product;
c) isolating the linked product as a solid;
d) purifying this solid; and
e) releasing the oligosaccharide from the polyethylene glycol.
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Citations
9 Claims
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1. A process for the preparation of oligosaccharides which comprises:
- a) reacting a first reactant saccharide having at least one monosaccharide unit with a second reactant which is a polyethylene glycol monomethyl ether, the two reactants being linked through an ester linkage of dicarboxylic acid bound to a carbohydrate carboxyl;
b) subjecting the saccharide-polyethylene glycol monomethyl ether reaction product to a glycosylation reaction through a plurality of additions of a glycosylation agent having an activated anomeric center, while monitoring the reaction for completion; c) isolating the polyethylene glycol-oligosaccharide as a solid; d) purifying the solid; and e) releasing the oligosaccharide from the polyethylene glycol. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9)
- a) reacting a first reactant saccharide having at least one monosaccharide unit with a second reactant which is a polyethylene glycol monomethyl ether, the two reactants being linked through an ester linkage of dicarboxylic acid bound to a carbohydrate carboxyl;
Specification