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Separation Of Glycans By Mixed-mode Liquid Chromatography

A glycan and chromatography technology, applied in the field of separating glycans by mixed-mode liquid chromatography, can solve problems such as poor resolution and achieve the effect of excellent resolution

Active Publication Date: 2014-06-25
DIONEX CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This zwitterionic column suffers from the disadvantage of showing relatively poor resolution for glycan groups with the same charge

Method used

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  • Separation Of Glycans By Mixed-mode Liquid Chromatography
  • Separation Of Glycans By Mixed-mode Liquid Chromatography
  • Separation Of Glycans By Mixed-mode Liquid Chromatography

Examples

Experimental program
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Effect test

example 1

[0167] Example 1. Preparation of Compound 10

[0168] Dimethylamine (2) was mixed with excess triethylamine (2.0 equivalents) in anhydrous CH 2 Cl 2 Mix in medium and maintain between about 0°C and about 5°C for 20 minutes. Add one dropwise in CH 2 Cl 2 10-undecenoyl chloride (1) (1.0 equiv) in , and the mixture was stirred at ambient temperature for 12 hours. The reaction mixture was washed with water, washed with Na 2 SO 4 Dry and remove the solvent in vacuo to yield compound 3. An excess of methyldiethoxysilane (4) (10 equivalents) was added to compound 3, followed by a catalyst solution (0.1 mol %) (eg, hexachloroplatinic acid in minimal ethanol). After stirring at 50 °C for 24 hours, residual silane and solvent were removed in vacuo to provide compound 10. Figure 7 .

example 2

[0169] Example 2. Preparation of Compound 11

[0170] A solution of 11-bromo-1-undecene (5) at 5 °C in THF was added dropwise to a solution of dimethylamine (2) (10 equiv) in THF and the Stirring was continued for 12 hours. The volatiles were removed in vacuo and the residue partitioned in CH 2 Cl 2 with H 2 Between O, use Na 2 SO 4 Drying, which was followed by removal of solvent in vacuo afforded compound 6. An excess of methyldiethoxysilane (4) (10 equivalents) was added to compound 6, followed by a catalyst solution (0.1 mol%) (eg, hexachloroplatinic acid in a minimum of ethanol). After stirring at 50 °C for 24 hours, residual silane and solvent were removed in vacuo to afford silyl compound 11. Figure 7 .

example 3

[0171] Example 3. Preparation of Phase 21

[0172] Compounds 10 and 11 were mixed in toluene at a predetermined ratio. A predetermined amount of crude silica gel is then added to this solution while stirring until homogeneity is obtained. The reaction mixture was kept at reflux for 3 days. The resulting mixture was filtered, washed with acetone, and dried under vacuum at 50° C. for 5 hours to give the functionalized silica of composition 21 . A capping step with trialkylchlorosilanes and / or dialkyldichlorosilanes can also be combined to produce a packing material for chromatographic separations. Figure 7 .

[0173] In an exemplary experimental protocol, 18 g of Compound 10, 1 g of Compound 11, and 15 g of crude silica gel (particle size, 1.9-μm; pore size, Surface area, 225m 2 / g) was dispersed in 50 mL of toluene (anhydrous) in a 250-mL round bottom flask and mixed in toluene. A predetermined amount of crude silica gel is then added to this solution while stirring unt...

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Abstract

An exemplary multimodal chromatographic medium of the invention includes one or more strong anion exchange, weak anion exchange, strong cation exchange and / or weak cation exchange binding sites in combination with one or more reverse phase and / or hydrophilic interaction chromatography binding site. In an exemplary embodiment, the sites interact with one or more glycans in a mixture of glycans in a manner that allows separation of glycans in the mixture and analysis of the glycan mixture. The media are incorporated into devices and systems for chromatographic analysis. Also provided are methods of using the multimodal media of the invention to analyze glycans.

Description

Background of the invention [0001] Glycans are widely distributed in biological systems in free and conjugated forms as part of glycoproteins, glycolipids, and proteoglycans. They are involved in a broad range of biological and physiological processes including cognition, regulatory function, cellular communication, gene expression, stability and activity of protein therapeutics, cellular immunity, growth and development. The biological and physiological functions of glycans often depend on the structure and type of oligosaccharides attached to these proteins and lipids. The structures of glycans are quite diverse and complex due to post-translational modifications and physiological conditions. Therefore, it is highly challenging to analyze comprehensive glycan profiles (ie, glycomes) and determine the structures of glycans for clinical use. [0002] HPAEC-PAD (High Performance Anion Exchange Chromatography with Pulsed Amperometric Detection) was the first routine assay deve...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01D15/32B01D15/36B01D15/20G01N30/02
CPCC07K1/165B01J41/20G01N30/482C08B37/0063B01D15/3847B01J43/00G01N33/68B01J20/286B01J20/3285B01J2220/54B01D15/363B01D15/305B01D15/325B01D15/362
Inventor X·刘U·埃契C·A·波尔
Owner DIONEX CORP
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