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US 6,723,843 B2Granted
Oligosaccharide synthesis
AssigneeAlchemia Pty Ltd
InventorsIstvan Toth, Gyula Dekany, Barry Kellam
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Abstract
The invention provides a system for solid-phase synthesis of oligosaccharides, based on the discovery that a 2-substituted-1,3-dioxocycloalkyl linker group of general formula (I) can be used to couple saccharide groups of both the O-glycoside and N-glycoside type to a polymer support. The invention provides reagents, reagent kits and methods for solid-phase oligosaccharide synthesis.
Claims18
A resin-linker-saccharide support for solid-phase synthesis of oligosaccharides, comprising:
- (a) a resin;
- (b) a linker covalently attached to said resin;
- and
- (c) one or more saccharide groups covalently attached to said resin via said linker;
- wherein the support is a compound of formula I
- in which
- R1 is hydrogen or C1-4 alkyl;
- R2 is hydrogen or C1-4 alkyl;
- R′ is an amino sugar, a glycosylamine, or a glycosylamine of an oligosaccharide;
- a mono or oligosaccharide coupled through an alkyl-, substituted alkyl-, aryl-, substituted aryl-, cycloalkyl-, or substituted cycloalkyl-amino group;
- or a mono or oligosaccharide coupled through a carboxyalkyl-, substituted carboxyalkyl-, carboxyaryl-, substituted carboxyaryl-, carboxycycloalkyl-, or substituted carboxycycloalkyl-amino group;
- and
- R″ is an alkyl, substituted alkyl, aryl, substituted aryl, cycloalkyl, or substituted cycloalkyl spacer group that is directly coupled to the resin support or that is coupled to the resin via a functionality that is stable to conditions of oligosaccharide synthesis and cleavage.
10 more elements
A linker-saccharide complex, having formula II
- in which
- R1 is hydrogen or C1-4 alkyl;
- R2 is hydrogen or C1-4 alkyl;
- and
- R′ is an amino sugar, a glycosylamine, or a glycosylamine of an oligosaccharide;
- a mono or oligosaccharide coupled through an alkyl-, substituted alkyl-, aryl-, substituted aryl-, cycloalkyl-, or substituted cycloalkyl-amino group;
- or a mono or oligosaccharide coupled through a carboxyalkyl-, substituted carboxyalkyl-, carboxyaryl-, substituted carboxyaryl-, carboxycycloalkyl-, or substituted carboxycycloalkyl-amino group;
- and
- R″ is an alkyl, substituted alkyl, aryl, substituted aryl, cycloalkyl, or substituted cycloalkyl spacer group that comprises a functionality capable of reacting with a functionalized resin.
6 more elements
Dependencies are inferred from the claim text.