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Separating agent for optical isomer

a technology of optical isomers and separation agents, which is applied in the separation of optically active compounds, chemical/physical processes, and esterified saccharide compounds, etc., can solve the problems of unsuitable maintenance of analytical equipment, complicated replacement between organic solvent-based mobile phases and aqueous mobile phases, and significant differences in medical effects and toxicities between the two enantiomeric isomers. , to achieve the effect of minimizing uv absorption and high asymmetry recognition ability

Inactive Publication Date: 2003-07-31
DAICEL CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0025] According to the present invention, a polysaccharide derivative-based asymmetry recognition agent with high asymmetry recognition ability and minimized UV absorption, that is suitably used as a HPLC chiral stationary phase under a reversed phase condition using an aqueous mobile phase or in chiral CE field, chiral TLC field and the like can be provided.

Problems solved by technology

In the field of pharmaceutical preparations, particularly, in many cases, there are significant differences in medical effect and toxicity between the two enantiomeric isomers.
Since enantiomeric isomers have completely the same physical and chemical properties, they cannot be separated and analyzed by ordinary separation means.
Since the HPLC chiral stationary phase is frequently used under a reversed phase condition that is an aqueous mobile phase, frequent replacement between an organic solvent-based mobile phase and the aqueous mobile phase is complicated and unsuitable from the point of the maintenance of analytic equipment.
It might also lead to a wrong operation by the mixing of the mobile phases.
However, an asymmetry recognition agent having a substituent having large UV absorptive group as aromatic group had the disadvantage in that it is not applicable to, for example, thin-layer chromatography as described above, liquid chromatographic separation comprising adding the asymmetry recognition agent to a mobile phase, micelle dynamic chromatography that is one kind of capillary electrophoreses, and the like.

Method used

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  • Separating agent for optical isomer
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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0030] Production of Cellulose

[0031] Tris(cyclohexylcarboxylate)-Supported Filler and Packed Column

[0032] (1) Synthesis of Cellulose Tris(cyclohexylcarboxylate) (a) To 15 ml of N,N-dimethylacetamide (DMAc), 1.5 g of vacuum-dried lithium chloride was dissolved to prepare a DMAc / LiCl solution.

[0033] Under a nitrogen atmosphere, 15 ml of the above DMAc / LiCl solution and 15 ml of pyridine were added to 1.0 g of cellulose, and the resulting mixture was dipped in an oil bath at 100.degree. C. and stirred for 24 hrs. Thereafter, 4.8 g of chloride cyclohexylcarboxylate (C.sub.6H.sub.11COCl) (34 mmol, 1.8 equivalents) was added thereto and reacted for 16 hrs at 100.degree. C. The resulting solution was dripped in 200 ml of methanol and reprecipitated followed by centrifugal precipitation. As a result, the intended ester derivative (2.8 g, 93%) was obtained. The elemental analytic result of the resulting ester derivative (a) is shown in Table 1.

1TABLE 1 Elemental Analytic Result of Cellulose ...

applied example 1

[0052] The enantiomeric isomer separation columns obtained in Example 1 and Comparative Examples 1-2 were used to perform the evaluation of asymmetry recognition ability for racemic modifications 1 and 2 represented by the following formulae by a liquid chromatography of the following condition. The result is shown in Table 2.

[0053]

2 Example 1: H.sub.2O / MeOH = 2.8 (v / v) Mobile Phase Comparative Examples 1 and 2: MeOH Flow Velocity 0.5 ml / min Temperature 25.degree. C.

[0054]

3 TABLE 2 1 2 Separating Agent Separation Factor (.alpha.) Comparative Comparative Racemic Modification Example 1 Example 1 Example 2 Racemic Modification 1 1.64 1.0 1.37 Racemic Modification 2 1.16 1.0 1.0

example 2

[0055] Production of Cellulose Tris(cyclopentylcarboxylate)-Supported Filler and Packed Column

[0056] (1) Synthesis of Cellulose Tris(cyclopentylcarboxylate) (d)

[0057] To 15 ml of N,N-dimethylacetamide (DMAc), 1.5 g of vacuum-dried lithium chloride was dissolved to prepare a DMAc / LiCl solution.

[0058] Under a nitrogen atmosphere, 15 ml of the DMAc / LiCl solution and 15 ml of pyridine were added to 1.0 g of cellulose, and the mixture was dipped in a hot water bath at 100.degree. C. and stirred for 24 hrs. Thereafter, 4.4 g of chloride cyclopentylcarboxylate (33 mmol, 1.8 equivalent) was added thereto and reacted at 100.degree. C. for 16 hrs. The reaction dope was poured into 200 ml of MeOH and reprecipitated followed by centrifugal separation. As a result, the intended ester derivative was obtained (2.5 g, 90%). The elementary analytic result of (d) is shown in Table 3.

[0059] (2) Production of Filler With Cellulose Tris(cyclopentylcarboxylate-) Supported Thereon

[0060] To 10 ml of tetrah...

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Abstract

The present invention provides a separating agent for enantiomeric isomers having no large UV absorption as represented by an aromatic group and having high asymmetric recognizability, particularly, high asymmetric recognizability in an aqueous mobile phase, or a separating agent for enantiomeric isomers comprising a polysaccharide alicyclic ester derivative free from aromatic group as an effective component.

Description

[0001] The present invention relates to a separating agent for enantiomeric isomers, in particular, a separating agent suitably used for separating enantiomeric isomers in chromatography. More particularly, the present invention relates to a separating agent for enantiomeric isomers that can enantiomerically resolve many kinds chiral compounds with high separation factors in the analysis of pharmaceuticals, foods, agricultural chemicals, fragrants and the like.PRIOR ARTS[0002] Many organic compounds have enantiomeric isomers that have the same physical and chemical properties such as boiling point, melting point, solubility and the like but show a difference in the physiological activity that influences the living body of an organism. This difference in the physiological activity between enantiomeric isomers is attributable to the following. In most cases, proteins and carbohydrates that compose the organism are composed only of the one of the enantiomeric isomers so that they show ...

Claims

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Application Information

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IPC IPC(8): B01D15/08B01D15/38B01J20/22B01J20/24B01J20/281C07B57/00C08B3/00
CPCB01D15/3833B01J20/22B01J20/24B01J20/262B01J20/265G01N30/48B01J20/285B01J20/29B01J2220/54C07B57/00C07H13/02B01J20/281
Inventor OKAMOTO, YOSHIOYAMAMOTO, CHIYOKUBOTA, TAKATERU
Owner DAICEL CHEM IND LTD
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