Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Patent
1992-10-27
1997-06-17
Mullis, Jeffrey C.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
525 543, 536 187, 536103, 210656, C08F 800
Patent
active
056398247
DESCRIPTION:
BRIEF SUMMARY
FIELD OF INDUSTRIAL APPLICATION
The present invention relates to a chemically bonded body which comprises a cyclic oligosaccharide derivative which is extremely useful as a functional material for optical resolution, a separating agent or separating apparatus comprising said chemically bonded body, and a process for separation using said separating agent or separating apparatus.
PRIOR ART
The separating agents of the prior art comprising a polysaccharide derivative exhibit a high resolving power for various racemic modifications as a stationary phase in liquid chromatography. In the optical resolution of a racemic modification with the separating agent, it is believed to be essential that the higher-order structure of the polysaccharide derivative well fits to the structure of the racemic modification to cause effective adsorptive interaction between the polysaccharide derivative and the racemic modification. However, there are also compounds which can be difficultly resolved even by the use of a polysaccharide derivative having a high resolving power as a matter of fact.
The present inventors have made extensive studies to develop a separating agent which can resolve such difficultly resolvable compounds, with their attention being paid to cyclic oligo-saccharides which are composed of repeating units having the same structure as that of the repeating units of polysaccharide, but the number of repeating units of which is smaller than that of polysaccharide.
Although a material comprising a silane-treated silica gel and a cyclic oligosaccharide derivative physically supported thereon, beads of a cyclic oligosaccharide derivative and a material prepared by chemically bonding the 6-position hydroxyl group of a cyclic oligosaccharide to a silica gel treated with a silane treatment having a cyclic ether group at the ends and then being derivated have already been known as a stationary phase using the cyclic oligosaccharide derivative in chromatography, the resolving powers of these materials are insufficient (see U.S. Pat. No. 4,539,399 and Anal. Chem., 1990, 62, 1610).
DISCLOSURE OF THE INVENTION
For the purpose of solving the above problem, the present inventors have made extensive studies on the preparation of cyclic oligosaccharide derivatives and the resolving powers thereof and have accomplished the present invention.
Namely, the present invention provides a chemically bonded body comprising a support and a cyclic oligosaccharide derivative, at least one of the 2-, 3- and 6-position hydroxyl groups of which is chemically bonded to the support through a spacer (with the proviso that those wherein the 6-position hydroxyl group is bonded to a support through an ether linkage are excepted), a separating agent or separating apparatus comprising said chemically bonded body and a process for separation using said separating agent or separating apparatus.
The spacer includes carbamates, esters and ethers, when the 2- or 3-position hydroxyl group of the oligosaccharide derivative is chemically bonded to a support, while it includes carbamates and esters, when the 6-position hydroxyl group thereof is chemically bonded to a support.
The hydroxyl groups of the cyclic oligosaccharide derivative to be used as the raw material are classified into three groups, i.e., a group of hydroxyl groups bonded to the spacer, a group of hydroxyl groups replaced with functional groups other than the spacer, and a group of unreplaced free hydroxyl groups. Now, the hydroxyl groups not bonded to the spacer will be described.
The cyclic oligosaccharide derivative to be used in the present invention is preferably one prepared by replacing part or the whole of the hydroxyl groups of a cyclic oligosaccharide which is composed of D-glucopyranoside repeating units as represented by the following general formula (1) by functional groups having 1 to 30 carbon atoms: ##STR1## (wherein n is an integer of 5 to 13)
The present invention will now be described in detail.
CYCLIC OLIGOSACCHARIDE
The cyclic oligosaccharide to be used in the
REFERENCES:
patent: 4426292 (1984-01-01), Wernick et al.
patent: 4539399 (1985-09-01), Armstrong
patent: 5104547 (1992-04-01), Cabrera et al.
patent: 5183809 (1993-02-01), Weisz et al.
Derwent Publications Ltd., London, GB; AN 89-042618 & JP-A-63314201, Japan Organo KK, "Fixing Cyclodextrin For Chromatographic Separate Filler Etc.", Dec. 22, 1988, Abstract (1 page).
Derwent Publications Ltd., London, GB; AN 86-321583 & JP-A-61237057, Toyo Soda Mfg. KK, "Filler For Liquid Chromatography", Oct. 22, 1986, Abstract (1 page).
File Supplier PAJ/JPO & JP-A-1053152, Tosoh Corp, "Packing Material For Liquid Chromatography", Mar. 1, 1989, Abstract (1 page).
Armstrong et al. "Derivatized Cyclodextring for Normal Phase Liquid Chromatographic Separation of Enantiomers", Anal. Chem. 62, 1610-1615, (Aug. 1990).
Daicel Chemical Industries Ltd.
Mullis Jeffrey C.
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