Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1995-01-11
1996-12-24
Kunz, Gary L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
436527, 436529, 502404, 502405, 536 56, 536 58, 536 63, C08B 312, C08B 330, C08B 1510, C08B 3104, B01J 2010
Patent
active
055874673
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The present invention relates to a separating agent for optical isomers and a process for producing the same. More particularly, it relates to a separating agent, which is obtained by crosslinking polysaccharide derivative molecules only among themselves on a support and useful as an optical resolution reagent for racemic modifications, and a process for producing the same.
DESCRIPTION OF RELATED ART
It is known that a column packing composed of silica gel having a polysaccharide derivative supported thereon is useful as a separating agent for optical isomers of a racemic modification (Y. Okamoto, M. Kawashima and K. Hatada, J. Am. Chem. Soc., 106, p.5357, 1984). However, such a separating agent is poor in solvent resistance since it comprises silica gel having a polysaccharide derivative which is supported on the silica gel simply by coating alone. When the separating agent is used as a column packing for liquid chromatography, therefore, some eluents cannot be used.
Accordingly, a separating agent which is composed of a support having a polysaccharide derivative supported thereon and has an excellent solvent resistance has been required.
SUMMARY OF THE INVENTION
The present inventors have conducted extensive studies on a separating agent whereby the above-mentioned problems can be solved without deterioration of the excellent characteristics of a polysaccharide derivative and, as a result, completed the present invention.
Thus, the present invention provides a separating agent for optical isomers which is characterized by being composed of a polysaccharide derivative which has been immobilized on a support through crosslinkage of polysaccharide derivative molecules only among themselves on the support, a process for producing the separating agent for optical isomers of the present invention which is characterized by crosslinking polysaccharide derivative molecules only among themselves on a support with the use of a polyfunctional crosslinking agent, a use of the separating agent for optical isomers of the present invention as a column packing for chromatography, and a process for separating a mixture of optical isomers which comprises separating the mixture of optical isomers from each other by using the separating agent for optical isomers according to the present invention.
DETAILED DESCRIPTION OF THE INVENTION
Although the polysaccharide in the present invention may be any of a synthetic polysaccharide, a natural polysaccharide and a modified natural polysaccharide without restriction, so long as it is optically active, those having a high regularity in the mode of binding are preferable. Examples of the polysaccharide include .beta.-1,4-glucan (cellulose), .alpha.-1,4-glucan (amylose, amylopectin), .alpha.-1,6-glucan (dextran), .beta.-1,6-glucan (bustulan), .beta.-1,3-glucan (e.g., curdlan, schizophyllan, etc.), .alpha.-l,3-glucan, .beta.-1,2-glucan (crown gall polysaccharide), .beta.-1,4-galactan, .beta.-1,4-mannan, .alpha.-1,6-mannan, .beta.-1,2-fructan (inulin), .beta.-2,6-fructan (levan), .beta.-1,4-xylan, .beta.-1,3-xylan, .beta.-1,4-chitosan, .beta.-1,4-N-acetylchitosan (chitin), pullulan, agarose and alginic acid. In addition thereto, starches containing amylose and the like are involved in the category of polysaccharides. Among them, those which can be easily obtained in a highly pure state, for example, cellulose, amylose, .beta.-1,4-chitosan, chitin, .beta.-1,4-mannan, .beta.-1,4-xylan, inulin and curdlan, are preferable and cellulose and amylose are preferable in particular.
The number-average degree of polymerization (the average number of pyranose or furanose rings per molecule) of the polysaccharide is 5 or above, preferably 10 or above. Although the upper limit of the number-average degree of polymerization of the polysaccharide is not particularly defined, it is preferable that the number-average degree of polymerization thereof does not exceed 500 from the viewpoint of workability.
An example of the polysaccharide derivative to be used in the present
REFERENCES:
patent: 4040022 (1978-05-01), Tsao et al.
J. Am. Chem. Soc., vol. 106, pp. 5357-5359, 1984.
Ichida Akito
Murakami Tatsushi
Daicel Chemical Industries Ltd.
Kunz Gary L.
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