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Monosaccharide polymer enrichment material and its preparation and application in glycopeptide enrichment

A technology for polymers and monosaccharides, which is used in analytical materials, preparation methods for peptides, preparation of samples for testing, etc., and can solve the problems of low glycosylation coverage, damage to sugar chains, and the need to improve selectivity.

Inactive Publication Date: 2019-06-25
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, lectin affinity chromatography has the problem of low glycosylation coverage [Kubota, et al. Anal. Chem. 2008]; hydrazine chemistry has high selectivity for glycopeptides, but destroys sugar chains [Zhang, H.; et al. Nat.Biotechnol.2003.]; Hydrophilic interaction chromatography is universal for glycopeptides, but the selectivity needs to be improved, so comprehensive glycoproteomics of complex biological samples cannot be realized

Method used

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  • Monosaccharide polymer enrichment material and its preparation and application in glycopeptide enrichment
  • Monosaccharide polymer enrichment material and its preparation and application in glycopeptide enrichment
  • Monosaccharide polymer enrichment material and its preparation and application in glycopeptide enrichment

Examples

Experimental program
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Effect test

Embodiment 1

[0064] Synthesis of Glucose Functional Monomer

[0065] Add 200ml of acetic anhydride solution into the reaction vessel, add 1ml of perchloric acid, slowly add 20g of required glucose, stir for 30min, put it in an ice bath, add 6g of red phosphorus, 20ml of bromine, and 14ml of water in turn, and then stir for 4h at room temperature . The resulting mixture was filtered, dried, and then washed three times with 50% petroleum ether ether solution, and spin-dried to obtain a glucose derivative in which other hydroxyl groups were brominated at the first position and protected by acetyl groups;

[0066] Add 20g of the above product into the reaction vessel, dissolve it with 150ml of chloroform, then add 150ml of saturated sodium carbonate solution, add 5g of tetrabutylammonium iodide, 8g of p-hydroxybenzaldehyde, react at 60 degrees Celsius for 12h, then remove the water layer, After drying, the mixture is purified by column chromatography. The first position is connected with p-hy...

Embodiment 2

[0073] Preparation of glycopolymer films

[0074]

[0075] In sugar polymers, x:0.01~0.5

[0076] Taking x=0.2 as an example, add 2g polyacrylamide and 0.5g monosaccharide functional monomer to a 50mL flask successively, add 10mL H2O and 15mL methanol as solvent at the same time, stir at 60°C for 48 hours, and the obtained product is mixed with methanol and After three days of dialysis in a mixed solution of water, the monosaccharide polymer was obtained as a white solid after freeze-drying.

[0077] Glycopolymer Characterization Data 1H NMR (500MHz, D2O): δ(ppm): 1.62(m, 20H, C-CH2), 2.20(d, 10H, C-CH), 3.39-3.96(m, 5H, CH- OH and CH2-OH), 4.21(t, J=3.0Hz, 1H, CH-OH), 5.43(d, J=8.1Hz, 1H, O-CH-O), 7.21(m, 2H, Ph-H ),7.89(d,J=7.1Hz,2H,Ph-H),9.75(s,1H,CH=N).IR(cm-1):3346,3202,2927,1658,1606,1579,1510, 1452,1429,1399,1350,1322,1257,1172,1115,1102,1072,1036,912,838,821,804,701,611.

[0078] Si, SiO2, Au, Ag, Pt, CuO, Al2O3, TiO2, ZrO2 or Fe3O4 connected with isothiocyanate...

Embodiment 3

[0080] Preparation of Glycopolymer Silica Functional Surface

[0081] Immerse the porous silica gel with isothiocyanate groups in the aqueous solution containing the above-mentioned monosaccharide aggregate; control the temperature of the flask at 60°C and let it stand for 4-6 hours; after the reaction, wash the polymer graft with methanol and H2O in sequence Porous silica gel was dried under vacuum at 30°C and placed in a desiccator for later use. The same method can be used to prepare silica gel samples grafted with smart glycopolymers with different particle sizes (including silica gel particle size and pore size), which can be used as packing materials for glycopeptide enrichment and separation columns. Figure 4 It is a picture of thermogravimetric analysis, a comparison chart of silica gel connected with sugar smart polymer and silica gel connected with isothiocyanate group;

[0082]

[0083] Structure and Synthetic Method of Functional Monomer

[0084] In order to pr...

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Abstract

The present invention relates to a monosaccharide polymer enrichment material and its preparation and application in glycopeptide enrichment. The monosaccharide functional monomer is copolymerized onto the polymer main chain through the method of Schiff base condensation, and further grafted onto the matrix material , to obtain a sugar-responsive polymer material; the monosaccharide polymer enrichment material is used in the enrichment and / or selective separation of glycopeptides; the matrix material modified by the polymer is contacted with the glycoprotein hydrolyzate, and then enriched Glycopeptides. The specific operation adopts solid phase extraction mode or dispersed solid phase extraction mode; when using monosaccharide polymer modified matrix material to enrich glycopeptides in solid phase extraction (SPE) mode, the glycoprotein hydrolyzate is added to the monosaccharide polymer The modified matrix material is filled with SPE, washed with eluent to remove non-glycopeptides, and glycopeptides are separated by eluent; the polymer modified material prepared by the present invention shows high selectivity when separating and enriching glycopeptides With the characteristics of high performance and high throughput, it can realize the selective enrichment of glycopeptides.

Description

technical field [0001] The present invention relates to sugar-responsive polymers, monosaccharide functional monomers, and monosaccharide grafted surfaces. At the same time, it also involves the separation and enrichment of glycopeptides, that is, the application of sugar-responsive polymer modification materials in the separation and enrichment of glycopeptides. Compared with the conventional enrichment method of hydrophilic interaction chromatography (HILIC), the polymer-modified material has the advantages of high selectivity, high adsorption capacity and high recovery when enriching glycopeptides. In addition, the enrichment can be carried out in the solid phase extraction column (SPE) mode or the dispersed solid phase extraction mode, which is simple to operate, high in throughput, and good in repeatability, and is suitable for the selective separation and enrichment of glycopeptides in complex systems. Background technique [0002] Glycosylation of proteins regulates ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J20/286B01D15/10B01J20/30G01N1/40C08G81/00C07K1/14
CPCB01D15/10B01J20/286B01J2220/54C07K1/145C08G81/00G01N1/405
Inventor 梁鑫淼孙涛垒李秀玲卿光焱姜舸熊雨婷
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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