Application of 2-phenyl-3-(p-aminophenyl)acrylonitrile as matrix in analyzing carbohydrates through MALDI-MS (Matrix Assisted Laser Desorption Ionization-Mass Spectrometry)

An aminophenyl, acrylonitrile technology, applied in the analysis of materials, material analysis by electromagnetic means, instruments, etc., can solve the problems of low ionization efficiency and inhibition, achieve simple synthesis, improve selectivity, and improve the degree of ionization Effect

Active Publication Date: 2018-08-14
JILIN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The invention provides the application of PAPAN as a matrix in the analysis of sugars by MALDI-MS. PAPAN derivatizes sugars through non-reductive amination reaction, thereby improving the ionization efficiency of sugars. In particular, PAPAN has strong absorption at 355nm and can be used as a matrix It assists the ionization of sugars, so the over-reacted derivatization reagent does not need to be separated. When MALDI-MS analyzes sugars, the use of PAPAN as a matrix not only improves the sensitivity of sugar detection, but also improves the selectivity of sugar detection, solving the problem of sugars. The problem of low ionization efficiency in MALDI and often suppressed by other samples

Method used

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  • Application of 2-phenyl-3-(p-aminophenyl)acrylonitrile as matrix in analyzing carbohydrates through MALDI-MS (Matrix Assisted Laser Desorption Ionization-Mass Spectrometry)
  • Application of 2-phenyl-3-(p-aminophenyl)acrylonitrile as matrix in analyzing carbohydrates through MALDI-MS (Matrix Assisted Laser Desorption Ionization-Mass Spectrometry)
  • Application of 2-phenyl-3-(p-aminophenyl)acrylonitrile as matrix in analyzing carbohydrates through MALDI-MS (Matrix Assisted Laser Desorption Ionization-Mass Spectrometry)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Synthesis and analysis of PAPAN, the synthesis schematic diagram of PAPAN is as follows figure 1 As shown, the specific steps are as follows:

[0028] 1. First add 20mL of methanol and 0.115g, 0.005mol of metallic sodium into a round bottom flask, mix and stir until the metallic sodium is completely dissolved into sodium methoxide. Then add 1.17g, 0.01mol phenylacetonitrile, and 1.51g, 0.01mol p-nitrobenzaldehyde, stir the mixture at room temperature for 2h until the reaction of the raw materials is complete to form a yellow precipitate, and the filtered solid is washed three times with methanol and water to obtain 2.25g Bright yellow product.

[0029] 2. Add 2.5g, 0.01mol of the bright yellow product prepared in step 1, 40mL of ethanol and 11.3g, 0.05mol of stannous chloride dihydrate SnCl in a round bottom flask 2 2H 2 O, the mixture was refluxed for 0.5h. with saturated NaHCO 3 Neutralize to slightly alkaline, dilute with 50mL of water, then extract w...

Embodiment 2

[0031] Example 2: PAPAN is used as a reactive matrix for the detection of maltohexaose by MALDI-MS.

[0032] 1. Prepare 10mM maltohexaose mother solution (aqueous solution), which can be stored in a refrigerator at 4°C.

[0033] 2. Configure 2.5g / L PAPAN solution in Example 1, the solvent used is methanol solution containing 5% acetic acid. It can be stored in a refrigerator at 4°C, protected from light.

[0034] 3. Take 99 μL of the PAPAN solution in step 2 into a 1.5 mL centrifuge tube, then add 1 μL of the maltohexaose mother liquor in step 1, mix well, and place it in a 65°C water bath for 1 hour.

[0035] 4. Take 0.5 μL of the reaction solution in step 3 and spot it on the anchorchip target plate, and immediately take 0.5 μL of pure water and spot it on the reaction solution, and let it dry naturally at room temperature.

[0036] 5. As a comparison, the mother liquor of maltohexaose in step 1 was diluted to 10 -4 M, take 1 μL maltohexaose solution and 1 μL common substra...

Embodiment 3

[0039] Example 3. Comparison of crystal morphology formed by two spotting methods when PAPAN is used as a matrix.

[0040] 1. Take 0.5 μL of the reaction solution in Example 2 and spot it on the anchorchip target plate, then immediately take 0.5 μL of pure water and spot it on the reaction solution, before the reaction solution dries, let it dry naturally at room temperature.

[0041] 2. Take 0.5 μL of the reaction solution in Example 2 and spot it on the anchorchip target plate, and let it dry naturally at room temperature.

[0042] 3. Send the target plate into MALDI-MS to observe its morphology.

[0043] Figure 5 The figure on the left is the MALDI-MS self-contained microscope morphology image obtained by applying the method of step 1 in Example 3, Figure 4 The right side is the morphological diagram obtained by spotting the method in step 2 of Example 3. It can be seen that the spotting method adopted in the present invention forms more uniform crystals than the common...

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Abstract

The invention relates to application of 2-phenyl-3-(p-aminophenyl) acrylonitrile as a matrix in analyzing carbohydrates through MALDI-MS (Matrix Assisted Laser Desorption Ionization-Mass Spectrometry). 2-phenyl-3-(p-aminophenyl) acrylonitrile as a reactive matrix for analyzing the carbohydrates through the MALDI-MS has high sensitivity and high selectivity, so that the problems that the ionizationefficiency of the carbohydrates in MALDI is low and the carbohydrates are often inhibited by other samples are solved. 2-phenyl-3-(p-aminophenyl)acrylonitrile can undergo non-reductive amination reaction with the aldehyde group of the carbohydrates and further can be used as a carbohydrate derivatization reagent so as to improve the ionization efficiency of the carbohydrates in the MALDI-MS; on the other hand, 2-phenyl-3-(p-aminophenyl)acrylonitrile also can be used as an MALDI matrix for assisting desorption ionization of the carbohydrates.

Description

technical field [0001] The invention relates to the field of biochemical detection, in particular to 2-phenyl-3-(p-aminophenyl) acrylonitrile (2-phenyl-3-(p-aminophenyl) acrylonitrile, PAPAN) as a matrix in matrix-assisted laser desorption ionization Application of time-of-flight mass spectrometry (Matrix Assisted Laser Desorption Ionization Mass Spectrometry, MALDI-MS) in the analysis of sugars. Background technique [0002] As a kind of soft ionization biological mass spectrometry, MALDI-MS technology has developed rapidly since Tanaka et al. reported it in 1988. It has the characteristics of high sensitivity, high throughput, high salt tolerance, and simple sample preparation. Therefore, in the analysis of biological samples, Environmental analysis, clinical and other aspects play an important role. In the MALDI-MS technique, the matrix forms a co-crystal with the analyte, and the matrix absorbs laser energy and transmits it to the analyte to assist in the analysis and i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N27/62
CPCG01N27/628
Inventor 国新华玲玲姜世梅马瑶
Owner JILIN UNIV
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