CN101411973A - Fixed phase of chiral ligand exchange chromatograph and its preparing process - Google Patents
Fixed phase of chiral ligand exchange chromatograph and its preparing process Download PDFInfo
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- CN101411973A CN101411973A CNA2008101445187A CN200810144518A CN101411973A CN 101411973 A CN101411973 A CN 101411973A CN A2008101445187 A CNA2008101445187 A CN A2008101445187A CN 200810144518 A CN200810144518 A CN 200810144518A CN 101411973 A CN101411973 A CN 101411973A
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- 239000003446 ligand Substances 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000000741 silica gel Substances 0.000 claims abstract description 30
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 30
- 150000001413 amino acids Chemical class 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 150000001414 amino alcohols Chemical class 0.000 claims abstract description 4
- 150000004985 diamines Chemical class 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 230000002209 hydrophobic effect Effects 0.000 claims description 7
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical group C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 claims description 6
- 125000003700 epoxy group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 claims description 3
- 239000005052 trichlorosilane Substances 0.000 claims description 3
- 239000005046 Chlorosilane Substances 0.000 claims 2
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims 2
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims 2
- 239000004593 Epoxy Substances 0.000 claims 1
- 229910008051 Si-OH Inorganic materials 0.000 claims 1
- 229910006358 Si—OH Inorganic materials 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 238000006459 hydrosilylation reaction Methods 0.000 claims 1
- 239000007790 solid phase Substances 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N serine Chemical compound OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 abstract 2
- 150000001261 hydroxy acids Chemical class 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- 230000005526 G1 to G0 transition Effects 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229960002429 proline Drugs 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 8
- 229930182821 L-proline Natural products 0.000 description 7
- 229940024606 amino acid Drugs 0.000 description 7
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000001291 vacuum drying Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 3
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical class O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 3
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Chemical compound OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- HQBKFSFXKKNIDP-QRPNPIFTSA-N (2s)-2-amino-3-(4-hydroxyphenyl)propanoic acid;2-amino-3-(4-hydroxyphenyl)propanoic acid Chemical compound OC(=O)C(N)CC1=CC=C(O)C=C1.OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 HQBKFSFXKKNIDP-QRPNPIFTSA-N 0.000 description 1
- BWKMGYQJPOAASG-VIFPVBQESA-N (3s)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid Chemical compound C1=CC=C2CN[C@H](C(=O)O)CC2=C1 BWKMGYQJPOAASG-VIFPVBQESA-N 0.000 description 1
- IJVQJMKMTUIHCF-DDWIOCJRSA-N 3-amino-3-phenylpropanoic acid (3R)-3-amino-3-phenylpropanoic acid Chemical compound OC(=O)CC(N)C1=CC=CC=C1.OC(=O)C[C@@H](N)C1=CC=CC=C1 IJVQJMKMTUIHCF-DDWIOCJRSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 206010019133 Hangover Diseases 0.000 description 1
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- 229930182844 L-isoleucine Natural products 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229940093740 amino acid and derivative Drugs 0.000 description 1
- -1 amino acid enantiomers Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention relates to a chiral ligand exchange chromatogram solid phase for splitting a chiral compound, in particular for splitting a chiral compound of amino acid, amino alcohol, hydroxy acid, glycol, diamine and other bidentate ligands, and belongs to the field of analytical chemistry. An amino acid chiral selector is bonded on the surface of silica gel subjected to hydrophobization treatment to prepare the chiral ligand exchange chromatogram solid phase. The chiral ligand exchange chromatogram solid phase has the advantages of simple method, high selectivity, high column efficiency, good symmetry of chromatographic peak and rapid splitting speed when a DL-amino acid enantiomer is split. The attached graph of abstract is a spectrogram which is formed through splitting DL-Serine on a chromatographic column.
Description
Technical field
The present invention is fixedly phase and preparation method thereof of a kind of chiral ligand exchange chromatograph, should fixing be used for high performance liquid chromatography resolving chiral compound mutually, particularly the amino acid of resolving chiral, amino alcohol, carboxylic acid, two pure and mild diamines etc. have the compound of bidentate, belong to the analytical chemistry field.
Background technology
Chiral ligand exchange chromatograph developed so far since nineteen seventies, obtained remarkable progress, now become a kind of method of very useful resolving chiral compound, particularly embodied unique advantages aspect many group compounds such as amino acid and derivative thereof, carboxylic acid, amino alcohol splitting.Chiral ligand exchange chromatograph can be divided into three types: 1) chirality bonded stationary phase (chiral stationary phases, CSP); 2) chirality be coated with the stain fixedly phase (chiral coated phases, CCP); 3) chirality flow phase (chiralmobile phases, CMP).
The ligand exchange chromatograph of the mobile phase of chirality is that certain metal ion species (is used Cu usually
2+) chiral coordination compound add to and flow mutually, fixedly carry out the fractionation of enantiomer on the phase (as ODS) at a kind of achirality, flow mutually, consumed the chooser of chirality owing to when test sample, chooser need be joined, increased the detection cost, be restricted thereby use.Davankov (Chromatographia, 1980,667) etc. 13 (11): respectively N-alkyl-L-hydroxy-proline and N-alkyl-L-hydroxy-proline are coated with and steep on anti-phase ODS post, prepared and be coated with fixedly phase of stain chiral ligand exchange chromatograph, can be directly used in amino acid whose fractionation.Wang Qunbiao etc. (Chinese patent ZL 99117305.8) are with (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid is the chirality chooser, prepared two kinds and be coated with fixedly phase of stain type chiral ligand exchange chromatograph, split some amino acid whose enantiomers with these two kinds of chiral stationary phases.Wang Shengqing etc. (Chinese patent ZL 200510020617.0) have synthesized N, S-two (2-hydroxyl-3-normal octane oxygen base) propyl group-(L)-cysteine, and it is coated with steeps on reverse-phase chromatography bonded stationary phase, prepared and be coated with fixedly phase of stain type chiral ligand exchange chromatograph, some amino acid are split, and have higher post to imitate.G ü bitz in 1981 etc. (J Chromatogr (A), 1981,203:377) at first developed fixedly phase of silica gel bonded chiral ligand exchange chromatograph.(analytical chemistry such as Wu Banggui; 1991; 19 (3); 291) with (Chinese ChemicalLetters such as L-proline, Chen Taos; 1995; 6 (5): 383) with (SCI, 2001,22 (4) such as L-hydroxyproline, Long Yuande; 565) with (S)-1; 2,3, (chromatograms such as 4-tetrahydroisoquinoline-3-carboxylic acid, Huang Xiaojia; 2003; 21 (3): 230) with the reaction of L-isoleucine and epoxidised silica gel, the chiral ligand exchange chromatograph that has prepared bonding type is phase fixedly, and some amino acid enantiomers are split.But the bonding type fixedly post of phase is imitated lowlyer, and the chromatographic peak hangover is serious.
Chirality is coated with fixing always the showing than higher post mutually of stain type and imitates and since the chirality chooser with fixing be that so combination is insecure, post is imitated loss seriously, and poor repeatability, and is very unstable with the hydrophobic interaction combination between two alkyl between mutually.And the chirality bonding type fixedly the chirality chooser of phase at fixing the more firm of combination of going up mutually, can under multiple mobile phase condition, use, and the fractionation to amino acid enantiomer is effective, but bonding type fixedly the post of phase imitate all very lowly always, can't be widely used.
Summary of the invention
The present invention is by imitating silica gel surface modification and the post that adopts closed-end technology to improve bonded stationary phase.The modification on silica gel surface mainly is that the Si on complete hydroxylated Bio-sil surface-OH base is converted into Si-H base, we again on the silica gel surface bond bigger alkyl make silica gel surface form the hydrophobic environment of one deck.The chiral ligand exchange chromatograph that has obtained a kind of Gao Zhuxiao is phase fixedly.The fixing collection mutually that the present invention makes is coated with stain the type fixedly Gao Zhuxiao and the fixing high stability mutually of bonding type of phase, obtained imitating and good peak shape than higher post by the fractionation to DL-amino acid and RS-carboxylic acid.
The present invention fixedly preparation method of phase is as follows: earlier silica gel and dimethylchlorosilane (dichlorosilane or trichlorosilane also can) be reacted, the compound that on the silica gel surface bond, has epoxide group then, hydrophobic alkyl on the silica gel surface bond afterwards, with the epoxide group reaction on chooser and silica gel surface, must arrive fixedly phase of chirality ligand exchange chromatograph at last.
Description of drawings
Fig. 1～Fig. 4 is respectively DL-β-Phenylalanine (β-phenylalanine), DL-Phenylalanine (phenylalanine), DL-Proline (proline), DL-Tyrosine (tyrosine) and goes up the spectrogram that splits in chromatographic column (I).
The specific embodiment
The concrete implementation step of fixedly phase of the present invention is as follows:
1, silica gel hydrogenation is with CCl
4Make solvent, make catalyst with pyridine.The Bio-sil that adds activation and dimethylchlorosilane (dichlorosilane or the trichlorosilane also can) 2～10h that refluxes after the reaction end, uses toluene, methyl alcohol-water and methanol wash successively.Just obtain silane glue.
2, the bonding linking arm joins in the flask with the rare hydrocarbon that contains epoxide group with the Bio-sil that alkyl will be connected Si-H key; make catalyst with chloroplatinic acid; isopropyl alcohol is a solvent, uses nitrogen protection, adds rare hydrocarbon continuation reaction 1～48h behind reaction 2～72h down at 10～85 ℃.Reaction is used isopropyl alcohol and methanol wash after finishing successively, and is standby after the vacuum drying then.
3, the bonded chiral chooser is solvent with methyl alcohol, adds the silica gel and the chirality chooser of bonding epoxide group, at 20～80 ℃ of following stirring reaction 2～72h.Use methyl alcohol, methyl alcohol-water and methanol wash successively, vacuum drying then must be arrived chirality bonded stationary phase.Promptly get chiral stationary phase chromatography post of the present invention after the dress post.
Embodiment 1
(1) at 40ml CCl
4The middle pyridine 2.0ml that adds silica gel 2.0g, dimethylchlorosilane 2.0ml, drying adds hot reflux 5h, and reaction is used toluene, methyl alcohol-water and methanol wash after finishing successively, obtains hydrogenation silica gel after the drying.
(2) in the 40ml isopropyl alcohol, add hydrogenation silica gel that step (1) obtains and the pi-allyl glycerin ether 2.0ml that contracts, add chloroplatinic acid 1mg, after adding thermal response 24h under 40 ℃, add 1-octene 2.0ml and continue reaction 6h.Reaction is used isopropyl alcohol and methanol wash after finishing successively, and dry back is standby.
(3) in 40ml methyl alcohol, add L-proline 1.12g (10mmol) and sodium methoxide 0.54g (10mmol), the dissolving back adds the product that step (2) obtains, at room temperature react earlier 12h, be heated to 60 ℃ of reaction 12h again, use methyl alcohol, methyl alcohol-water and methanol wash successively, after the vacuum drying, just obtain L-proline bonded stationary phase.Promptly get chiral stationary phase chromatography post of the present invention (I) after the dress post.
Embodiment 2
(1) at 40ml CCl
4The middle pyridine 2.0ml that adds silica gel 2.0g, dimethylchlorosilane 2.0ml, drying adds hot reflux 5h, and reaction is used toluene, methyl alcohol-water and methanol wash after finishing successively, obtains hydrogenation silica gel after the drying.
(2) in the 40ml isopropyl alcohol, add hydrogenation silica gel that step (1) obtains and the pi-allyl glycerin ether 2.0ml that contracts, add chloroplatinic acid 1mg, after adding thermal response 24h under 40 ℃, add styrene 0.5ml and continue reaction 6h.Reaction is used isopropyl alcohol and methanol wash after finishing successively, and dry back is standby.
(3) in 40ml methyl alcohol, add L-proline 1.12g (10mmol) and sodium methoxide 0.54g (10mmol), the dissolving back adds the product that step (2) obtains, at room temperature react earlier 12h, be heated to 60 ℃ of reaction 12h again, use methyl alcohol, methyl alcohol-water and methanol wash successively, after the vacuum drying, just obtain L-proline bonded stationary phase.Promptly get chiral stationary phase chromatography post of the present invention (II) after the dress post.
Embodiment 3
(1) at 40ml CCl
4The middle pyridine 2.0ml that adds silica gel 2.0g, dimethylchlorosilane 2.0ml, drying adds hot reflux 5h, and reaction is used toluene, methyl alcohol-water and methanol wash after finishing successively, obtains hydrogenation silica gel after the drying.
(2) in the 40ml isopropyl alcohol, add hydrogenation silica gel that step (1) obtains and the pi-allyl glycerin ether 2.0ml that contracts, add chloroplatinic acid 1mg, after adding thermal response 20h under 40 ℃, add cyclohexene 2.0ml and continue reaction 8h.Reaction is used isopropyl alcohol and methanol wash after finishing successively, and dry back is standby.
(3) in 40ml methyl alcohol, add L-proline 1.12g (10mmol) and sodium methoxide 0.54g (10mmol), the dissolving back adds the product that step (2) obtains, at room temperature react earlier 12h, be heated to 60 ℃ of reaction 12h again, use methyl alcohol, methyl alcohol-water and methanol wash successively, after the vacuum drying, just obtain L-proline bonded stationary phase.Promptly get chiral stationary phase chromatography post of the present invention (III) after the dress post.
Claims (6)
1, the fixing phase of a kind of chiral ligand exchange chromatograph, be used for the resolving chiral compound, particularly the amino acid of resolving chiral, amino alcohol, carboxylic acid, two pure and mild diamines have the compound of bidentate, it is characterized in that the amino acid chiral chooser is bonded on the silica gel surface of handling through hydrophobization, the chiral ligand exchange chromatograph of preparation Gao Zhuxiao is phase fixedly.
2, the fixing phase of a kind of chiral ligand exchange chromatograph according to claim 1, it is characterized in that the hydrophobization processing is meant that elder generation makes the Si-OH of silica gel surface hydrophilic be converted into hydrophobic Si-H in silica gel and chlorosilane reaction, then the silica gel surface of hydrophobic R group generation Si-R form on the bonding.
3, the fixing phase of a kind of chiral ligand exchange chromatograph according to claim 1, it is characterized in that the amino acid chiral chooser is bonded to the lip-deep method of silica gel is: the Si-H that will contain the epoxy linking arm of two keys and silica gel surface earlier carries out hydrosilylation and is bonded on the silica gel surface, and reaction is connected to the silica gel surface to epoxide group with the amino acid chiral chooser more then.
4, the fixing phase of a kind of chiral ligand exchange chromatograph according to claim 2 is characterized in that chlorosilane is dimethylchlorosilane, dimethyl dichlorosilane (DMCS) and trichlorosilane.
5, according to the fixing phase of the described a kind of chiral ligand exchange chromatograph of claim 2, it is characterized in that hydrophobic R group is C
1～C
20Alkyl and hydrophobic grouping such as aromatic radical.
6, the fixing phase of a kind of chiral ligand exchange chromatograph according to claim 3, the length that it is characterized in that linking arm is C
4～C
20
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102614847A (en) * | 2011-01-28 | 2012-08-01 | 中国科学院大连化学物理研究所 | Amphoteric ion hydrophilic chromatographic stationary phase and preparation method thereof |
| CN102614846A (en) * | 2011-01-28 | 2012-08-01 | 中国科学院大连化学物理研究所 | Strong anion exchange chromatographic stationary phase and preparation method thereof |
| CN102614845A (en) * | 2011-01-28 | 2012-08-01 | 中国科学院大连化学物理研究所 | Strong cation exchange chromatographic stationary phase and preparation method thereof |
| CN104289210A (en) * | 2014-07-02 | 2015-01-21 | 苏州苏凯路化学科技有限公司 | Preparation method of novel phenylalanine chiral chromatographic column stationary phase |
| CN104558255A (en) * | 2015-01-30 | 2015-04-29 | 北京理工大学 | Cyclodextrin derivative containing oxazoline segments as well as preparation and application of hydrogenated silica gel stationary phase bonded with cyclodextrin derivative |
-
2008
- 2008-07-23 CN CNA2008101445187A patent/CN101411973A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102614847A (en) * | 2011-01-28 | 2012-08-01 | 中国科学院大连化学物理研究所 | Amphoteric ion hydrophilic chromatographic stationary phase and preparation method thereof |
| CN102614846A (en) * | 2011-01-28 | 2012-08-01 | 中国科学院大连化学物理研究所 | Strong anion exchange chromatographic stationary phase and preparation method thereof |
| CN102614845A (en) * | 2011-01-28 | 2012-08-01 | 中国科学院大连化学物理研究所 | Strong cation exchange chromatographic stationary phase and preparation method thereof |
| WO2012100592A1 (en) * | 2011-01-28 | 2012-08-02 | 中国科学院大连化学物理研究所 | Zwitterionic hydrophilic chromatography stationary phase and manufacturing method thereof |
| CN102614846B (en) * | 2011-01-28 | 2013-09-18 | 浙江华谱新创科技有限公司 | Strong anion exchange chromatographic stationary phase and preparation method thereof |
| CN102614845B (en) * | 2011-01-28 | 2013-12-18 | 浙江华谱新创科技有限公司 | Strong cation exchange chromatographic stationary phase and preparation method thereof |
| CN102614847B (en) * | 2011-01-28 | 2013-12-18 | 浙江华谱新创科技有限公司 | Amphoteric ion hydrophilic chromatographic stationary phase and preparation method thereof |
| US9138721B2 (en) | 2011-01-28 | 2015-09-22 | Dalian Institute Of Chemical Physics, Chinese Academy Of Sciences | Zwitterionic stationary phase for hydrophilic interaction liquid chromatography and preparation method thereof |
| CN104289210A (en) * | 2014-07-02 | 2015-01-21 | 苏州苏凯路化学科技有限公司 | Preparation method of novel phenylalanine chiral chromatographic column stationary phase |
| CN104558255A (en) * | 2015-01-30 | 2015-04-29 | 北京理工大学 | Cyclodextrin derivative containing oxazoline segments as well as preparation and application of hydrogenated silica gel stationary phase bonded with cyclodextrin derivative |
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Application publication date: 20090422 |