Catalytic antibodies hydrolyzing acylated carbohydrates in a regioselective and stereoselective manner
AssigneeProtein Engineering Research Institute
InventorsIkuo Fujii, Yoshiharu Iwabuchi, Hideaki Miyashita
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Abstract
A method of regio-and stereoselective hydrolysis to deprotect an acylated hydroxy group in acylated carbohydrates, which contributes to synthesis of complex oligosaccharides, is provided. The method utilizes catalytic antibodies as hydrolase.
Claims17
A method for hydrolytically deprotecting an acylated hydroxy group in a carbohydrate in a regioselective and stereoselective manner, which comprises the step of:
- admixing a catalytically effective amount of a catalytic antibody with the carbohydrate containing the acylated hydroxy group, wherein the catalytic antibody specifically hydrolyzes the acylated hydroxy group in the carbohydrate in a regioselective and stereoselective manner, thereby deprotecting the acylated hydroxy group in the carbohydrate in a regioselective and stereoselective manner,
- said catalytic antibody being produced by immunizing an animal using a compound, as a hapten, which is thought to be a transition state analog of desired hydrolysis of the carbohydrate containing the acylated hydroxy group.
A catalytic antibody produced by immunizing an animal with a compound of the following formula:
- ##STR20## as a hapten.
A hybridoma 17E11 (FERM P-13824).
A method for producing an oligosaccharide, which comprises the steps of:
- (a) preparing a protected carbohydrate comprising a monosaccharide or an oligosaccharide by acylation of all hydroxy groups in the monosaccharide or oligosaccharide with a carboxyl compound,
- (b) admixing a catalytically effective amount of a catalytic antibody with the monosaccharide or oligosaccharide, wherein the catalytic antibody specifically hydrolyzes a single acylated hydroxy group in the monosaccharide or a single acylated hydroxy group at a non-reducing end of the oligosaccharide in a regioselective and stereoselective manner, thereby deacylating the single acylated hydroxy group in the monosaccharide or oligosaccharide in a regioselective and stereoselective manner, and
- (c) covalently bonding another monosaccharide or oligosaccharide to the deacylated hydroxy group of the monosaccharide or oligosaccharide obtained in step (b),
- said catalytic antibody being produced by immunizing an animal using a compound, as a hapten, which is thought to be a transition state analog of desired hydrolysis of the carbohydrate containing the acylated hydroxy group.
Dependencies are inferred from the claim text.