Liquid purification or separation – With means to add treating material – Chromatography
Patent
1993-06-02
1999-05-04
Therkorn, Ernest G.
Liquid purification or separation
With means to add treating material
Chromatography
2105021, 210635, 210656, 502403, B01D 1508
Patent
active
059001445
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE ART
The present invention relates to an optical isomer separating agent which comprises a support and conalbumin bonded thereto and to a high-performance liquid chromatographic column packed with the separating agent.
BACKGROUND ART
It is known that only one of the optical isomers constituting a racemic modification has a physiological activity in the natural world. It has recently been found in the field of drugs that only one of the optical isomers constituting a racemic modification has a remarkable pharmacological effect or a low toxicity in some cases, for which the development of a drug with an isolated optical isomer has risen in importance.
Only a few methods for the separation of optical isomers can be practically conducted on an industrial scale, though many methods therefor have been known hitheroto. Therefore, a method which can separate optical isomers easily and at a low cost has been sought. In recent years, with the progress in high-performance liquid chromatography, methods for separating optical isomers have become known generally and separatory columns having various performances have also been reported.
However, there are only a few columns usable for the separation of optical isomers while it is known that very many compounds have optical isomers. In addition, not all optical isomers can always be efficiently separated, and therefore the development of a new separatory column has been expected.
DISCLOSURE OF THE INVENTION
The present inventors have extensively studied to develop an optical isomer separating agent having a new separating ability. As a result, they have found that the above object can be attained by taking the following constitution. The present invention has been accomplished on the basis of this finding.
Namely, the present invention relates to an optical isomer separating agent characterized by being composed of a stationary phase comprising a support and conalbumin or chemically modified conalbumin bonded to the support. Further, the present invention also relates to a high-performance liquid chromatographic column packed with an optical isomer separating agent characterized by being composed of a stationary phase comprising a support and conalbumin or chemically modified conalbumin bonded to the support.
According to the present invention, optical isomers which could not be separated or could only be insufficiently separated according to the prior art can be efficiently separated. Accordingly, an object of the present invention is to provide a new optical isomer separating agent which has a new optical isomer separating ability and a high-performance liquid chromatographic column packed with this new separating agent.
The support in the present invention refers to a fine support to which conalbumin can be chemically bonded, and examples thereof include silica gel, glass, cellulose, synthetic polymers and aminopropyl silica gel.
Conalbumin is a protein falling under the category of albumins and its molecular weight is 70,000 (or 87,000 according to some other reports). The pH of the isoelectric point thereof is 5.8. It exists in egg white and accounts for 13.8% of the proteins constituting the egg white.
The conalbumin used may be a commercially available one. Alternatively, the conalbumin may be prepared from egg white by a known process (Kagaku Daijiten (Encyclopaedia Chimica), Vol. 3, p.744 (1977)).
Conalbumin can be bonded to a support by a conventional process for the preparation of a stationary phase. For example, when aminopropyl silica gel is used as the support, the bonding of the conalbumin can be conducted by using N,N-disuccinimidyl carbonate as a crosslinking agent. Further, when silica gel is used as the support, the bonding of the conalbumin can be conducted by using 3-glycidoxypropyltrimethoxysilane as a crosslinking agent.
The chemically modified conalbumin in the present invention refers to conalbumin which is partially chemically converted by cross-linkage with glutaraldehyde, conversion into diol, acylation or modification with
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Mikes' Laboratory Handbook of Chromatographic and Allied Methods, John Wiley & Sons, New York, 1979, pp. 402 and 403.
Hand Journal of Chromatography, vol. 603, 1992, Amsterdam, pp. 105-109.
Asakawa Naoki
Mano Nariyasu
Miwa Toshinobu
Oda Yoshiya
Sato Tadashi
Eisai Co. Ltd.
Therkorn Ernest G.
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