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 Polysaccharide substances, process for producing them and use of them

Details
Inventors: Okamoto, Yoshio; Enomoto, Naoki; Furukawa, Sachiko; Ogasawara, Yasushi; Akano, Hirofumi; Kawamura, Yoshiya;
Assignee: Nakano Vinegar Co., Ltd. (Handa, JP)
Primary Examiner: Griffin; Ronald W.
Assistant Examiner:
Attorney, Agent or Firm: Frishauf, Holtz, Goodman, Langer & Chick

A polysaccharide substance having the following formula is provided: ##STR1## Also provided is a method of producing the polysaccharide substance in which an oligosaccharide having a degree of polymerization from 3 to 10 is chemically bonded to a silane agent at the reducing terminal of the resultant oligosaccharide, the oligosaccharide compound is then polymerized to an average degree of polymerization from 11 to 500 in the presence of an enzyme. Another method for producing the polysaccharide substance is provided in which an aldehyde group at the reducing terminal of an oligosaccharide having a degree of polymerization from 3 to 10 is oxidized with an oxidizing agent, and the saccharide chain of the oxidized product is polymerized to a degree of polymerization from 11 to 500 in the presence of an enzyme, followed by the addition of an acid. The polysaccharide substance has excellent solvent resistance and is useful as a separating agent for chromatography, especially for the separation of chiral compounds.

DETAILED DESCRIPTION Accordingly, there is provided in accordance with the present invention a novel substance having a main structure of the following Formula (1) in which a polysaccharide or a derivative thereof is chemically bonded to the inner and outer surfaces of a porous carrier at the reducing terminal of said polysaccharide or derivative thereof.
##STR5## [wherein R represents Ra, --CO--Ra or --CO--NH--Ra (in which Ra represents a hydrogen atom or a substituent selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group and a substituted or unsubstituted heterocyclic residue); on the point of improving separation ability remarkably, substitution rate of R is preferably 30 to 100%.
Rb represents a substituted or unsubstituted methylene group, a substituted or unsubstituted phenylene group or a group containing covalently bonded hetero atom(s); Z represents a member selected from the group consisting of the surface of a porous carrier, a halogen atom, an alkyl group, an alkoxy group, a phenyl group, a silane agent and a saccharide-bonded silane agent; m.
sub.
1 represents the number of monosaccharide units, which may be in the range of from 10 to 500 on average; and m2 represents an integer of from 1 to 20].
Also provided are a method of producing the novel substance of the above Formula (1) in which an oligosaccharide having a degree of polymerization from 3 to 10 is chemically bonded to a silane agent at the reducing terminal of the oligosaccharide, the oligosaccharide derivative obtained is extended to an average degree of polymerization from about 11 to about 500 by the action of an enzyme, and then the resulting polysaccharide is chemically bonded to a porous carrier at the silane moiety present at the terminal of the polysaccharide; a method of producing the novel substance of the above Formula (1) in which the aldehyde group present at the reducing terminal of an oligosaccharide having a degree of polymerization from 3 to 10 is oxidized with an oxidizing agent, and the saccharide chain of the oxidized product is polymerized to a degree of polymerization about 11 to about 500 by the action of an enzyme, followed by the addition of an acid; and a separating agent for chromatography comprising the novel substance represented by Formula (1)



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