Biological micromolecule or its analogue bonded chiral stationery phase

A chiral stationary phase and bonding technology, applied in other chemical processes, chemical instruments and methods, etc., can solve problems such as lack of stability of bidentate structure

Inactive Publication Date: 2006-11-22
劳文剑 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The connecting arms of this stationary phase are all single-tooth str

Method used

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  • Biological micromolecule or its analogue bonded chiral stationery phase
  • Biological micromolecule or its analogue bonded chiral stationery phase
  • Biological micromolecule or its analogue bonded chiral stationery phase

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0063] A double-tooth structure connecting arm silica gel. The preparation method of chiral chromatographic stationary phase has two kinds, and a kind of is that linking arm and chiral selector react with silane coupling agent earlier, then couple on silica gel (William H.Pirkle, J.Chromatogr.A, 1992 , 589, 45). The other is to couple the silane coupling agent to the silica gel first, and then react with the connecting arm or the chiral selector to obtain the stationary phase (US Patent Publication No. US2004 / 0226889 A1). The latter preparation method is preferred in the present invention. Silica gel is coupled with a silylating reagent. To 4.0 g of pretreated silica gel (Kromasil, 5 μm, 100 Å, Switzerland), 120 mL of dry toluene and 30 mL of bis(trimethoxysilylpropyl)amine (Gelest, Inc., Morrisville, PA.USA) were added. Under nitrogen protection, heat in an oil bath at 140°C for 24 hours. After cooling, filter, wash the solid with toluene and acetone, and dry it in vacuum ...

Embodiment 2

[0066]In 20 mL of anhydrous DMF, add 3.8 grams of bonded silica gel in Example 1, 4 grams of HATU (Sigma-Aldrich Corp. St. Louis, MO, USA) and 1.4 grams of DIPEA (Sigma-Aldrich Corp. St. Louis, MO , USA), and then added 4.0 g of fluorenylmethoxycarbonyl-protected proline (Fmoc-Pro-OH) (CHEM-IMPEX INTERNATIONAL, IL, USA). After stirring for 12 hours, it was filtered and the silica gel was washed with DMF, methanol and dichloromethane. The Fmoc protecting group was reacted with 20 mL of piperidine in 20% DMF for 60 minutes to remove it. Filter and wash the solid with DMF and dichloromethane. dry. This is the first coupling process. After the obtained silica gel was subjected to the same coupling twice, the obtained silica gel was added to 20 mL of dichloromethane, and then 1.6 g of DIPEA and 1.4 g of trimethylacetyl chloride (Sigma-Aldrich Corp. St. Louis, MO, USA) were added. After stirring for 12 hours, it was filtered and the solid was washed with DMF, methanol and dichlo...

Embodiment 3

[0072] According to the method of Example 1, 3-aminopropyl silica gel was prepared. For the synthesis of amino-bonded silica for longer chain monodentate linkers, in anhydrous DMF, add 4.0 g of this bonded silica, 750 mg of DIC (Sigma-Aldrich Corp. St.Louis, MO, USA), 800 mg HOBT (Sigma-AldrichCorp.St.Louis, MO, USA) and 700 mg of 4-(1-Boc piperidine) acetic acid (Sigma-AldrichCorp.St.Louis, MO, USA), stirred for 12 hours, filtered, and used for silica gel DMF, methanol and dichloromethane washes. The Boc protecting group was removed with 50% trifluoroacetic acid in dichloromethane for 60 minutes, and the solid was treated with DMF, dichloromethane and 50% N,N-diisopropylethylamine (DIPEA) (Sigma-Aldrich Corp.St .Louis, MO, USA) dichloromethane solution washes, and dries, obtains the amino-bonded silica gel of the monodentate connecting arm of long chain. According to the method of Example 2, using Fmoc-Pro-OH, after three times of coupling and end-capping, the stationary ph...

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Abstract

The invention relates to a process of preparing chiral fixed phase bonded by biomicromolecule or its analogues. It is characterized in that the connection arm bonded on carrier comprises ring structure or side chain, which bonds chiral selective agent through conjugated linkage or electrovalent bond. The ring structure or side chain on connection arm is double dentation or single dentation with side chain. The biomicromolecule or its analogues are chiral selective agent, and comprise 2-20 L or D proline, alpha-substituted proline or hydroxyproline and their analogues. The invention is suitable for high efficiency liquid chromatography, preparative chromatography, analog moving bed, microcylinder liquid chromatography and capillary electrochromatography.

Description

technical field [0001] The invention relates to a chiral stationary phase bonded to small biomolecules or analogs thereof and a preparation method thereof. Biological small molecules or their analogs bonded chiral chromatography column stationary phase is a kind of chiral separation material, and the preparation method adopts organic synthesis technology, especially solid phase synthesis technology. Background technique [0002] Chiral separation analysis methods and techniques are becoming more and more important, especially in the fields of chemistry, biology, environmental science, fine chemicals, pharmaceuticals and various product quality inspections. Chromatography is the most important method for chiral separation, and currently mainly includes capillary gas chromatography, high performance liquid chromatography, supercritical fluid chromatography, capillary electrophoresis, and electrochromatography. The direct chiral separation method is chiral separation with chir...

Claims

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Application Information

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IPC IPC(8): B01J20/29
Inventor 劳文剑
Owner 劳文剑
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