JPH09236581A - Optical splitting agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To enable optical splitting by using a specific compd. in the dummy fixing phase of electrokinetic chromatography. SOLUTION: A compd. represented by formula (wherein R, R<1> , R<2> , R<5> and R<6> are respectively specific groups) is used in the dummy fixing phase of electrokinetic chromatography being one of separation techniques by a capillary electrophoretic method and the concn. thereof may be within a range from crytical micelle concn. to solvent soluble concn. but, pref., a capillary is filled with the compd. as a 5-50mM aq. soln. Subsequently, a 0.01MNaOH aq. soln. containing an object to be analyzed is injected into the capillary and voltage is applied across both ends of the capillary to perform separation. As a support electrolyte soln. for electrokinetic chromatography, a sodium tetraborate aq. soln. or a phosphate buffer soln. is designated but it may be appropriately selected corresponding to a compd. to be separated.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to electrokinetic chromatography.

[0002]

2. Description of the Related Art Capillary electrophoresis (Capillary El
ectrophoresis: Hereinafter referred to as CE. ) Has been in the spotlight in recent years as a means having a resolution superior to that of the conventional separation analysis method.

Electrokinetic Chromatography (CE), which is one of the separation methods by CE,
Expressed as EKC. ) Is a method in which the coexistence of a “pseudo stationary phase”, which is an ionic substance that interacts with the compound to be separated, in the supporting electrolyte solution is used to perform separation analysis by utilizing the difference in the degree of the interaction. is there. Terabe et al. Used sodium dodecylsulfate (hereinafter referred to as SDS) as a pseudo stationary phase and used a method utilizing the difference in the incorporation method of the compound to be separated into micelles formed by SDS, that is, micelle electrokinetic chromatography (Micellar Electrokinetic Chroma
tography: Hereafter referred to as MEKC. ) (Anal.Chem., 5
6 , 111 (1984)). Many attempts have been made with this as a starting point, and there are also reports of separation of optically active compounds by MEKC.

In order to achieve optical resolution by MEKC,
Asymmetric discrimination needs to be performed in the process in which the compound to be separated interacts with the pseudo stationary phase, and therefore an optically active surfactant is used for the pseudo stationary phase. As an optically active surfactant, bile salts (J. Chromatogr., 480 , 403 (198
9)), various glycosides (J. Liq. Chromatogr., 16 , 933 (199
3)) and other "natural" optically active surfactants, as well as amino acid derivatives (Anal. Chem., 61 , 1984 (1989), etc.), sugar derivatives (A
Nal. Chem., 66 , 4121 (1994)) and other "non-natural" optically active surfactants have been reported.

[0005]

However, in reality, even if these surfactants are used as the optical resolving agent, the optical resolving is often impossible by itself. In some compounds, optical resolution may be achieved by allowing other substances to coexist in the optical resolving agent, but most compounds cannot be resolved.

[0006]

Means for Solving the Problems Accordingly, the present inventors have:
The present invention has been completed by finding that optical resolution can be achieved by using the compound of the general formula (I) as a pseudo stationary phase of EKC.

The compound of the general formula (I) is described in JP-A 1-22
It is disclosed in 1387 and JP-A-6-25273.

The compound of the general formula (I) is a compound related to lipid A, and more specifically, a lipid A derivative and a derivative of a reducing subunit of the two subunits constituting lipid A.

[0009] Lipid A is a phospholipid moiety constituting a substance called lipopolysaccharide (LPS) existing in the outermost layer of the cell wall of Gram-negative bacteria, and is known to exhibit various biological activities. Lipid A depends on the bacterial species
Although the type, number and binding position of fatty acids are different, the basic structure is a disaccharide amine with a fatty acid residue and a phosphate linked, and consists of a reducing subunit and a non-reducing subunit. For example, lipid A of E. Coli has the following structure.

[0010]

[Chemical 21] It is known that each of the subunits having the above structure exhibits an action similar to that of lipid A.

The compounds according to the invention have the general formula (I)

[0012]

Embedded image (Where R is

[0013]

Embedded image Or

[0014]

Embedded image Represents

R ¹ , R ² , R ³ and R ⁴ are each independently

[0016]

Embedded image Represents

Z ¹ is an alkylene group having 1 to 20 carbon atoms,
It means a phenylene group or a combination of an alkylene group having 1 to 20 carbon atoms and a phenylene group, and the alkylene group and / or the phenylene group may have a hydroxyl group. Z ² and Z ³ each independently represent an alkylene group having 1 to 20 carbon atoms, a phenylene group, or a combination of a linear or branched alkylene group having 1 to 20 carbon atoms and a phenylene group. Z ⁴ means an alkylene group having 1 to 9 carbon atoms.

R ⁷ means a cyclic alkyl group having 3 to 12 carbon atoms which may have one or more hydroxyl groups. Q ¹
Is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, -CONH
_2, refers to a -COOH or CH ₂ OH. Q ² is a hydrogen atom or a phenyl group, which may have 1 to 2 carbon atoms.
It means an alkyl group having 0 to 0, a phenyl group which may have an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 1 to 20 carbon atoms which may contain phenylene between them.
n means an integer of 0 to 10.

R ⁵ represents a hydrogen atom or a phosphono group. R ⁶ is a phosphono group or a formula

[0020]

Embedded image Means

M and t are each independently 0 to 6
Means an integer. Q ³ means a carboxyl group or a phosphonoxy group. Q ⁴ represents a hydrogen atom, a carboxyl group or a phosphonoxy group.

Q means a carboxyl group or a phosphonoxy group. Y means an alkylene group having 1 to 10 carbon atoms, and the alkylene group may have one or more substituents —OR ⁸ and / or substituents —NHR ⁹ . R ⁸ and R ⁹ are each independently —CO—Z ⁵
Or ^{-CO-Z 7 -N (Z 6} ) means a -CO-Z ⁸ -H.

Z ⁵ and Z ⁶ are each independently an alkyl group having 1 to 20 carbon atoms which may have a phenyl group, a phenyl group which may have an alkyl group having 1 to 20 carbon atoms, Or, it means an alkyl group having 1 to 20 carbon atoms which may include phenylene between them. Z ⁷ and Z
Each ⁸ independently represents a combination of an alkylene group having 1 to 20 carbon atoms and a phenylene group or one of them. ).

The present invention relates to a separation method characterized by using a compound represented by the general formula (I).

The present invention also relates to a method for separating an optically active compound, which comprises using the compound represented by the general formula (I).

Alternatively, it relates to a method for separating an optically active compound by electrokinetic chromatography, which is characterized by using a compound represented by the general formula (I).

It also relates to an optical resolving agent represented by the general formula (I).

Further, it relates to a compound for pseudo stationary phase of electrokinetic chromatography, which is represented by the general formula (I).

The present invention also relates to an optical resolving agent of the general formula (I) used in electrokinetic chromatography.

The compound used in the present invention may be used as a salt, for example, triethylamine, pyridine or N.
Examples thereof include salts with organic amines such as methylglucamine and tris (hydroxymethyl) aminomethane, and salts with inorganic salts such as ammonium, sodium, potassium, calcium and magnesium.

In order to achieve the object of the present invention, those having an optically active amphipathic structure, such as a lipid A derivative and a derivative of each subunit constituting lipid A, that is, an amino group and a phosphoric acid Any compound having a structure having both a hydrophilic part of a mono- or disaccharide part having a group, a carboxyl group or / and a sulfuric acid residue and a hydrophobic part of a plurality of long-chain fatty acid residue parts may be used.

Therefore, the compound used in the present invention is not limited to the compound represented by the general formula (I), and various lipid A derivatives and derivatives of each subunit constituting lipid A are mentioned below. It is conceivable that the lipid A derivative and the derivative of each subunit constituting lipid A, which are described in the literature and the like, can also undergo optical resolution similarly to the compound of the general formula (I).

As a derivative of lipid A, JP-A-59-
No. 48497, JP-A-61-53295 and JP-A-61-227586. Examples of the disaccharide derivative include a derivative in which a long-chain fatty acid residue portion is an unsaturated fatty acid having a double bond or a triple bond unsaturated bond (Japanese Patent Laid-Open No. 5-194470). Furthermore, a 6-position-substituted lipid A derivative having a substituent introduced at the 6-position has also been reported (JP-A-4-234895).
issue).

The derivative of the reducing end subunit is described in Japanese Patent Publication No. 60-501259. Also,
JP-A-1-146891 discloses a monophosphoryl lipid A derivative.

Regarding the derivative of the non-reducing terminal subunit, JP-A-61-26093 and JP-A-61-1 are available.
There is a report in No. 26094. Also known is a derivative in which the hydroxyl group at the 1-position is a hydrogen atom, JP-A-61-172867. Furthermore, the phosphoric acid residue at the 4-position is a sulfuric acid residue, and 5
Derivatives in which an aryl group is introduced into the chain or at the terminal of a hydroxymethyl group at the 2-position or a sulfoxymethyl group at the 2-position or an acyl group at the 3-position are known (Japanese Patent Laid-Open No. 64-52793 and Japanese Patent Laid-Open No. 52793/1992). Kaisho 363-17988
5).

Further, a glucopyranose derivative in which succinic acid or methyl succinate is introduced at the 6-position of the non-reducing subunit is disclosed in JP-A-62-129293, and JP-A-2-256697 discloses the non-reducing subunit. Of 6
A lipid A monosaccharide analog in which the position is protected with an aliphatic acyl group is disclosed. Non-reducing subunit 3
A derivative having a structure in which the position is acylated with an alkyl-substituted fatty acid is also known (JP-A-3-106894).

The compound capable of achieving optical resolution according to the present invention is not particularly limited, and examples thereof include compounds having a carboxyl group or a carboxyl residue, and further aromatic compounds having a carboxyl group or a carboxyl residue. As such a compound, for example, a derivative of an amino acid (a derivative having no aromatic ring can be optically derivatized by converting it to a fluorescent derivative by dansylation, etc.)
And new quinolone derivatives which have been used or studied as antibacterial agents.

The terms used in this specification will be described. The "optically active compound" is a compound having an asymmetric carbon. The “pseudo stationary phase” is an ionic substance that is placed in a supporting electrolyte solution for electrokinetic chromatography and interacts with a compound to be separated. “Optical resolving agent” means a compound having the ability to separate optical isomers.

Next, each substituent of the compound of the general formula (I) used in the present invention will be described. The alkylene group means methylene, polymethylene, or methylene or polymethylene substituted with an alkyl group having 1 to 6 carbon atoms, and the alkyl group means a straight chain alkyl or branched chain alkyl group.

R ¹ , R ² , R ³ and R ⁴ are each independently

[0041]

Embedded image The number of carbon atoms in these groups is preferably 8 or more (excluding the carbon atoms contained in the Q ¹ , Q ² and R ⁷ moieties).

In the above formula, Z ² and Z ³ have 1 to 6 carbon atoms.
Is preferred. R ⁷ is preferably a cyclic alkyl group having 5 to 8 carbon atoms. n is preferably an integer from 0 to 5.

As R ¹ , R ² , R ³ and R ⁴ ,

[0044]

Embedded image Is preferable, especially

[0045]

Embedded image Is preferred.

Specific examples of preferred R ¹ , R ² , R ³ and R ⁴ include tetradecanoyl (-CO (CH ₂ ) ₁₂ CH ₃ ) N-dodecanoylglycyl (-COCH ₂ NHCOCH (CH ₂ ) ₁₀ CH ₃ ) 8-benzoylaminooctanoyl (-CO (CH ₂ ) ₇ NHCOC ₆ H
₅₎ 6-octanoyl aminohexanoyl (-CO (CH _{2) 5} NHCO
_{(CH 2) 6 CH 3)} 6- benzoylamino-hexanoyl _{(-CO (CH 2) 5 NHCOC} 6 H
₅ ) and N-dodecanoyl sarcosyl (-COCH ₂ N (CH ₃ ) C
O (CH ₂ ) ₁₀ CH ₃ ).

Next, for R

[0048]

Embedded image The part represented by is described.

As Y, ethylene or propylene having a substituent —OR ⁸ and / or a substituent —NHR ⁹ is preferable. Further, as R ⁸ and R ⁹ , tetradecanoyl (-CO (CH ₂ ) ₁₂ CH ₃ ) N-dodecanoylglycyl (-COCH ₂ NHCOCH (CH ₂ ) ₁₀ CH ₃ ) 8-benzoylaminooctanoyl ( -CO (CH ₂ ) ₇ NHCOC ₆ H
₅₎ p-octanoyl-aminobenzoyl _{(-COC 6 H 4 NHCO (CH} 2)
₆ CH ₃ ) 6-octanoylaminohexanoyl (-CO (CH ₂ ) ₅ NHCO
_{(CH 2) 6 CH 3)} 6- benzoylamino-hexanoyl _{(-CO (CH 2) 5 NHCOC} 6 H
₅ ) and N-dodecanoyl sarcosyl (-COCH ₂ N (CH ₃ ) C
Those selected from the group consisting of O (CH ₂ ) ₁₀ CH ₃ ) are preferred.

A carboxyl group is preferable as Q.

In the present invention, ultraviolet rays (UV) as shown in FIG. 1 are used.
A capillary electrophoresis apparatus equipped with a detector (in some cases, a fluorescence detector) is used.

Examples of the supporting electrolyte solution for electrokinetic chromatography include various solutions such as an aqueous sodium tetraborate solution and a buffer solution such as a phosphate buffer solution, which may be appropriately selected depending on the compound to be separated. For example, in the case of separating an amino acid compound, a phosphate buffer or a sodium tetraborate aqueous solution is used, and when the compound to be separated is a quinolone derivative, a sodium tetraborax aqueous solution is used.

The pH of the supporting electrolyte depends on the supporting electrolyte to be used, but in the case of the phosphate buffer solution, the pH is 9.0 to 1
A solution of 0.2, preferably pH 9.1 to 9.5, is used.
When using sodium tetraborax aqueous solution pH 9.0 to 1
It is preferably 0.6, preferably pH 9.3 to 10.0.

The concentration of the supporting electrolyte varies depending on the supporting electrolyte to be used, but in the case of the phosphate buffer solution, it is 0.05 M to 0.20.
A solution of M, preferably 0.07 M to 0.15 M is used. When using sodium tetraborate aqueous solution 0.03 M to 0.20 M
, Preferably from 0.05 M to 0.15 M.

The concentration of the compound represented by the general formula (I) may be in the range of being more than the critical micelle concentration and soluble in the solvent, but it is preferably an aqueous solution of 5 mM to 50 mM and filled in the capillary. Then, a 0.01 M NaOH aqueous solution containing the analyte is injected into the capillary, and then voltage is applied to both ends of the capillary for separation.

The capillary electrophoresis apparatus, the material and size of the capillaries used, and the operating conditions are not particularly limited, but in the examples of the present application, experiments were conducted with the following apparatus and method under room temperature conditions.

Capillary: inner wall untreated fused silica tube, inner diameter: 50 μm, total length: 750 mm (effective length: 500 mm) Marking voltage: 10 kV Sample injection: drop method; 20 cm-5 seconds. Will be specifically described with reference to Examples, but the present invention is not limited thereto.

The structures of the compounds used in the examples are shown below.

[0059]

[Table 1]

[0060]

【Example】

Example 1 Optical Resolution of Ofloxacin Compound (1) was treated with 0.1 M sodium tetraborax aqueous solution (pH
A solution of 20 mM dissolved in 9.3) was used as a supporting electrolyte solution for electrokinetic chromatography, a sample was dissolved in 0.01 M NaOH aqueous solution, and the following compounds were subjected to optical resolution under the following conditions. The result is shown in FIG.

[0061]

Embedded image

[Division conditions] Supporting electrolyte solution: 0.1 M sodium tetraborate aqueous solution (pH 9.3) containing 20 mM of monomeglumine salt of compound (1) Detection wavelength: UV-295 nm

Example 2 Optical Resolution of Ofloxacin Analogue Compound (1) was added to a 0.1 M sodium tetraborax aqueous solution (pH).
9.3) to 13 mM to prepare a supporting electrolyte solution for electrokinetic chromatography, dissolve the sample in 0.01 M NaOH aqueous solution, and perform optical resolution for each of the following compounds under the conditions shown below. I asked. The degree of separation (Rs) was calculated from the following formula.

[0064]

[Equation 1] t _fast : the moving time of the peak of the antipode moving first t _slow : the moving time of the peak of the antipode moving later W _fast : Width of the peak of the antipode moving first W _slow : Width of the peak of the antipode moving later

[0065]

[Table 2]

[Division conditions] Supporting electrolyte solution: 0.1 M sodium tetraborate aqueous solution (pH 9.3) containing 13 mM of monomeglumine salt of compound (1) Detection wavelength: UV-295 nm

[0067]

[0068]

[Table 3]

Example 3 Optical Resolution of Quinolone Derivative Compound (1) was dissolved in 0.05 M sodium tetraborax aqueous solution (pH 9.6) to 13 mM to prepare a supporting electrolyte solution for electrokinetic chromatography, and a sample was prepared. To 0.0
The mixture was dissolved in a 1 M NaOH aqueous solution, and optical resolution was performed on the mixture of the compounds shown below under the conditions shown below. The result is shown in FIG.

[0070]

Embedded image

[Division conditions] Supporting electrolyte solution: 0.05 M sodium tetraborate aqueous solution (pH 9.) containing 13 mM of monomeglumine salt of compound (1).
6) Detection wavelength: UV-295 nm

Example 4 Optical resolution of dansyl leucine

[0073]

Embedded image

Compound (1) was dissolved in 0.1 M disodium hydrogen phosphate aqueous solution to 13 mM to prepare a supporting electrolyte solution for electrokinetic chromatography.
It was dissolved in an aqueous OH solution and subjected to optical resolution under the following conditions. FIG. 4 shows the results.

[Division conditions] Supporting electrolyte solution: 0.1 M disodium hydrogen phosphate aqueous solution containing 13 mM of monomeglumine salt of compound (1) Detection wavelength: UV-260 nm

Example 5 Optical Resolution of Dansyl Norleucine

[0077]

Embedded image

Compound (1) was dissolved in 0.1 M disodium hydrogen phosphate aqueous solution to 13 mM to prepare a supporting electrolyte solution for electrokinetic chromatography, and a sample of 0.01 M was used.
It was dissolved in a NaOH aqueous solution and subjected to optical resolution under the following conditions. The result is shown in FIG.

[Division conditions] Supporting electrolyte solution: 0.1 M disodium hydrogen phosphate aqueous solution containing 13 mM of monomeglumine salt of compound (1) Detection wavelength: UV-260 nm

Example 6 Optical resolution of ofloxacin Compound (2) was dissolved in 0.1 M sodium tetraborax aqueous solution (pH 9.3) to 13 mM to prepare a supporting electrolyte solution for electrokinetic chromatography. 0.01M
It was dissolved in a NaOH aqueous solution, and the following compounds were subjected to optical resolution under the conditions shown below. FIG. 6 shows the result.

[0081]

Embedded image

[Division conditions] Supporting electrolyte solution: 0.1 M sodium tetraborax aqueous solution (pH 9.3) containing 13 mM of compound (2) Detection wavelength: UV-295 nm

Example 7 Optical Resolution of Quinolone Derivatives Compound (3) was treated with 0.05 M sodium tetraborate aqueous solution (pH
9.6) was dissolved in the solution to 13 mM and used as a supporting electrolyte solution for electrokinetic chromatography.
After dissolving in an aqueous solution, a mixture of the compounds shown below was subjected to optical resolution under the conditions shown below. FIG. 7 shows the result.

[0084]

Embedded image

[Division conditions] Supporting electrolyte solution: 0.05 M containing 13 mM of compound (3)
Aqueous sodium borax solution (pH 9.6) Detection wavelength: UV-295 nm

Example 8 Optical Resolution of Quinolone Derivative Compound (4) was treated with a 0.1 M sodium tetraborax aqueous solution (pH
A solution of 13 mM dissolved in 9.3) was used as a supporting electrolyte solution for electrokinetic chromatography, a sample was dissolved in 0.01 M NaOH aqueous solution, and the mixture of the compounds shown below was subjected to optical resolution under the following conditions. FIG. 8 shows the result.

[0087]

Embedded image

[Division conditions] Supporting electrolyte solution: 0.1 M sodium tetraborax aqueous solution (pH 9.3) containing 13 mM of compound (4) Detection wavelength: UV-295 nm

Example 9 Optical Resolution of Dansyl Norleucine

[0090]

Embedded image

Compound (5) was dissolved in 0.05 M sodium tetraborax aqueous solution (pH 9.5) to 20 mM to prepare a supporting electrolyte solution for electrokinetic chromatography.
It was dissolved in 0.01 M NaOH aqueous solution, and optical resolution was performed under the following conditions. The result is shown in FIG.

[Division conditions] Supporting electrolyte solution: 0.05 M containing 20 mM of compound (5)
Aqueous sodium borax solution (pH 9.5) Detection wavelength: UV-260 nm

Example 10 Optical resolution of dansyltryptophan

[0094]

Embedded image

Compound (6) was dissolved in 0.05 M sodium tetraborax aqueous solution (pH 9.5) to 10 mM to prepare a supporting electrolyte solution for electrokinetic chromatography, and a sample was prepared.
It was dissolved in 0.01 M NaOH aqueous solution, and optical resolution was performed under the following conditions. The result is shown in FIG.

[Division conditions] Supporting electrolyte solution: 0.05 M containing 10 mM of compound (6)
Aqueous sodium borax solution (pH 9.5) Detection wavelength: UV-260 nm

Example 11 Optical resolution of ofloxacin analogs

[0098]

Embedded image

The compound (7) was dissolved in 0.05 M sodium tetraborax aqueous solution (pH 9.5) to 20 mM to prepare a supporting electrolyte solution for electrokinetic chromatography.
It was dissolved in 0.01 M NaOH aqueous solution, and optical resolution was performed under the following conditions. The result is shown in FIG.

[Division conditions] Supporting electrolyte solution: 0.05 M containing 20 mM of compound (7)
Sodium tetraborax aqueous solution (pH 9.5) Detection wavelength: UV-295 nm

Example 12 Optical resolution of kynurenine

[0102]

Embedded image

The compound (7) was dissolved in 0.05 M sodium tetraborate aqueous solution (pH 9.5) to 30 mM to prepare a supporting electrolyte solution for electrokinetic chromatography.
It was dissolved in 0.01 M NaOH aqueous solution, and optical resolution was performed under the following conditions. FIG. 12 shows the result.

[Division conditions] Supporting electrolyte solution: 0.05 M containing 30 mM of compound (7)
Aqueous sodium borax solution (pH 9.5) Detection wavelength: UV-240 nm

[0105]

[Brief description of drawings]

FIG. 1 is a schematic diagram showing the configuration of a general capillary electrophoresis apparatus for carrying out the present invention.

FIG. 2 is a chart showing the experimental results of Example 1.

FIG. 3 is a chart showing the experimental results of Example 3.

FIG. 4 is a chart showing experimental results of Example 4.

FIG. 5 is a chart showing the experimental results of Example 5.

FIG. 6 is a chart showing experimental results of Example 6.

FIG. 7 is a chart showing experimental results of Example 7.

FIG. 8 is a chart showing the experimental results of Example 8.

FIG. 9 is a chart showing experimental results of Example 9.

FIG. 10 is a chart showing experimental results of Example 10.

FIG. 11 is a chart showing the experimental results of Example 11

FIG. 12 is a chart showing the experimental results of Example 12

[Procedure amendment]

[Submission date] May 20, 1996

[Procedure 3]

[Document name to be amended] Drawing

[Correction target item name] All figures

[Correction method] Change

[Correction contents]

FIG.

[Fig. 2]

[Figure 3]

FIG. 4

[Figure 5]

FIG. 6

FIG. 7

[Figure 8]

[Figure 9]

FIG. 10

FIG. 11

FIG.

Continuation of the front page (51) Int.Cl. ⁶ Identification number Office reference number FI technical display location G01N 27/26 301B

Claims (5)

[Claims] 1. A compound of the general formula (I) (Wherein R is Or Represents R ¹ , R ² , R ³ and R ⁴ are each independently Represents Z ¹ represents an alkylene group having 1 to 20 carbon atoms, a phenylene group, or a combination of an alkylene group having 1 to 20 carbon atoms and a phenylene group, and the alkylene group and / or the phenylene group may have a hydroxyl group. Good. Z ² and Z ³ are each independently an alkylene group having 1 to 20 carbon atoms, a phenylene group, or 1 carbon atom.
To 20 combinations of alkylene and phenylene groups. Z ⁴ means an alkylene group having 1 to 9 carbon atoms. R ⁷ means a cyclic alkyl group having 3 to 12 carbon atoms, which may have one or more hydroxyl groups. Q ¹ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, -CONH ₂ , -CO
Means OH or —CH ₂ OH. Q ² is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a phenyl group,
It means a phenyl group which may have an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 1 to 20 carbon atoms which may contain phenylene between them. n means an integer of 0 to 10. R ⁵ represents a hydrogen atom or a phosphono group. R ⁶ is a phosphono group or has the formula Means m and t are each independently 0 to 6
Means an integer. Q ³ means a carboxyl group or a phosphonoxy group. Q ⁴ represents a hydrogen atom, a carboxyl group or a phosphonoxy group. Q means a carboxyl group or a phosphonoxy group. Y has 1 to 1 carbon atoms
0 means an alkylene group, which is a substituent —O
It may have one or more R ⁸ and / or the substituent —NHR ⁹ . R ⁸ and R ⁹ are each independently -C
It means OZ ⁵ or -CO-Z ⁷ -N (Z ⁶ ) -CO-Z ⁸ -H. Z ⁵ and Z ⁶ are each independently an alkyl group having 1 to 20 carbon atoms which may have a phenyl group, and 1 to 2 carbon atoms.
It means a phenyl group which may have an alkyl group of 0, or an alkyl group having 1 to 20 carbon atoms which may contain phenylene between them. Z ⁷ and Z ⁸ each independently represent a combination of an alkylene group having 1 to 20 carbon atoms and a phenylene group or one of them. ) A method for separating an optically active compound, characterized by using a compound represented by 2. The separation method according to claim 1, wherein the separation method is electrokinetic chromatography. 3. A compound represented by the general formula (I): (In the formula, R is Or Represents R ¹ , R ² , R ³ and R ⁴ are each independently Represents Z ¹ represents an alkylene group having 1 to 20 carbon atoms, a phenylene group, or a combination of an alkylene group having 1 to 20 carbon atoms and a phenylene group, and the alkylene group and / or the phenylene group may have a hydroxyl group. Good. Z ² and Z ³ are each independently an alkylene group having 1 to 20 carbon atoms, a phenylene group, or 1 carbon atom.
To 20 combinations of alkylene and phenylene groups. Z ⁴ means an alkylene group having 1 to 9 carbon atoms. R ⁷ means a cyclic alkyl group having 3 to 12 carbon atoms, which may have one or more hydroxyl groups. Q ¹ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, -CONH ₂ , -CO
Means OH or —CH ₂ OH. Q ² is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a phenyl group,
It means a phenyl group which may have an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 1 to 20 carbon atoms which may contain phenylene between them. n means an integer of 0 to 10. R ⁵ represents a hydrogen atom or a phosphono group. R ⁶ is a phosphono group or has the formula Means m and t are each independently 0 to 6
Means an integer. Q ³ means a carboxyl group or a phosphonoxy group. Q ⁴ represents a hydrogen atom, a carboxyl group or a phosphonoxy group. Q means a carboxyl group or a phosphonoxy group. Y has 1 to 1 carbon atoms
0 means an alkylene group, which is a substituent —O
It may have one or more R ⁸ and / or the substituent —NHR ⁹ . R ⁸ and R ⁹ are each independently -C
It means OZ ⁵ or -CO-Z ⁷ -N (Z ⁶ ) -CO-Z ⁸ -H. Z ⁵ and Z ⁶ are each independently an alkyl group having 1 to 20 carbon atoms, which may have a phenyl group, and 1 to 20 carbon atoms.
The phenyl group optionally having an alkyl group or an alkyl group having 1 to 20 carbon atoms which may contain phenylene therebetween. Z ⁷ and Z ⁸ each independently represent a combination of an alkylene group having 1 to 20 carbon atoms and a phenylene group or one of them. ) Optical resolving agent represented by 4. A compound represented by the general formula (I): (In the formula, R is Or Represents R ¹ , R ² , R ³ and R ⁴ are each independently Represents Z ¹ represents an alkylene group having 1 to 20 carbon atoms, a phenylene group, or a combination of an alkylene group having 1 to 20 carbon atoms and a phenylene group, and the alkylene group and / or the phenylene group may have a hydroxyl group. Good. Z ² and Z ³ are each independently an alkylene group having 1 to 20 carbon atoms, a phenylene group, or 1 carbon atom.
To 20 combinations of alkylene and phenylene groups. Z ⁴ means an alkylene group having 1 to 9 carbon atoms. R ⁷ means a cyclic alkyl group having 3 to 12 carbon atoms, which may have one or more hydroxyl groups. Q ¹ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, -CONH ₂ , -CO
Means OH or —CH ₂ OH. Q ² is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a phenyl group,
It means a phenyl group which may have an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 1 to 20 carbon atoms which may contain phenylene between them. n means an integer of 0 to 10. R ⁵ represents a hydrogen atom or a phosphono group. R ⁶ is a phosphono group or has the formula Means m and t are each independently 0 to 6
Means an integer. Q ³ means a carboxyl group or a phosphonoxy group. Q ⁴ represents a hydrogen atom, a carboxyl group or a phosphonoxy group. Q means a carboxyl group or a phosphonoxy group. Y has 1 to 1 carbon atoms
0 means an alkylene group, which is a substituent —O
It may have one or more R ⁸ and / or the substituent —NHR ⁹ . R ⁸ and R ⁹ are each independently -C
It means OZ ⁵ or -CO-Z ⁷ -N (Z ⁶ ) -CO-Z ⁸ -H. Z ⁵ and Z ⁶ are each independently an alkyl group having 1 to 20 carbon atoms which may have a phenyl group, and 1 to 2 carbon atoms.
It means a phenyl group which may have an alkyl group of 0, or an alkyl group having 1 to 20 carbon atoms which may contain phenylene between them. Z ⁷ and Z ⁸ each independently represent a combination of an alkylene group having 1 to 20 carbon atoms and a phenylene group or one of them. ),
Compounds for pseudo stationary phase of electrokinetic chromatography 5. A compound represented by the general formula (I): (In the formula, R is Or Represents R ¹ , R ² , R ³ and R ⁴ are each independently Represents Z ¹ represents an alkylene group having 1 to 20 carbon atoms, a phenylene group, or a combination of an alkylene group having 1 to 20 carbon atoms and a phenylene group, and the alkylene group and / or the phenylene group may have a hydroxyl group. Good. Z ² and Z ³ are each independently an alkylene group having 1 to 20 carbon atoms, a phenylene group, or 1 carbon atom.
To 20 combinations of alkylene and phenylene groups. Z ⁴ means an alkylene group having 1 to 9 carbon atoms. R ⁷ means a cyclic alkyl group having 3 to 12 carbon atoms, which may have one or more hydroxyl groups. Q ¹ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, -CONH ₂ , -CO
Means OH or —CH ₂ OH. Q ² is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a phenyl group,
It means a phenyl group which may have an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 1 to 20 carbon atoms which may contain phenylene between them. n means an integer of 0 to 10. R ⁵ represents a hydrogen atom or a phosphono group. R ⁶ is a phosphono group or a compound of the formula Means m and t are each independently 0 to 6
Means an integer. Q ³ means a carboxyl group or a phosphonoxy group. Q ⁴ represents a hydrogen atom, a carboxyl group or a phosphonoxy group. Q means a carboxyl group or a phosphonoxy group. Y has 1 to 1 carbon atoms
0 means an alkylene group, which is a substituent —O
It may have one or more R ⁸ and / or the substituent —NHR ⁹ . R ⁸ and R ⁹ are each independently -C
It means OZ ⁵ or -CO-Z ⁷ -N (Z ⁶ ) -CO-Z ⁸ -H. Z ⁵ and Z ⁶ are each independently an alkyl group having 1 to 20 carbon atoms which may have a phenyl group, and 1 to 2 carbon atoms.
It means a phenyl group which may have an alkyl group of 0, or an alkyl group having 1 to 20 carbon atoms which may contain phenylene between them. Z ⁷ and Z ⁸ each independently represent a combination of an alkylene group having 1 to 20 carbon atoms and a phenylene group or one of them. ),
Optical resolving agent for electrokinetic chromatography