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Application of N-methyl phenylethylamine and isotope reagent thereof in carboxyl compound detection

A carboxyl compound, methylphenethylamine technology, applied in the field of organic chemistry and analytical chemistry, can solve the problems of limited application scope, low detection throughput, complicated operation, etc., to achieve the effect of assisting screening and improving sensitivity

Inactive Publication Date: 2020-05-19
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the application range of the currently reported labeling reagents is relatively limited, and it is only suitable for labeling a class of carboxyl compounds. In order to realize the analysis and detection of various types of carboxy metabolites, several labeling reagents need to be used in combination, resulting in complex operations and low detection throughput.

Method used

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  • Application of N-methyl phenylethylamine and isotope reagent thereof in carboxyl compound detection
  • Application of N-methyl phenylethylamine and isotope reagent thereof in carboxyl compound detection
  • Application of N-methyl phenylethylamine and isotope reagent thereof in carboxyl compound detection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: MPEA and d 3 - Application of MPEA in the detection of short-chain carboxylic acids

[0030] d 3 - Synthesis of MPEA:

[0031] The first step: under anhydrous and oxygen-free conditions, add 10 mL of anhydrous tetrahydrofuran to a container containing 1.84 mmol of N-(2-phenylethyl) acetamide, stir until dissolved, then add sodium hydride (3.68 mmol) and stir 45min. Add iodomethane-d dropwise 3 (9.19 mmol), reacted overnight. The tetrahydrofuran was spin-dried in vacuo, followed by liquid-liquid extraction with dichloromethane and water. Continuous extraction was performed three times, dried over anhydrous sodium sulfate, the organic phases were combined and concentrated, and then subjected to column chromatography, the eluent was petroleum ether: ethyl acetate = 10:1. Finally, 172.4 mg of oily liquid was obtained.

[0032] Step 2: Dissolve the intermediate obtained above with 3 mL of ethylene glycol, add 0.2 mL of 10% dilute hydrochloric acid, and refl...

Embodiment 2

[0033] Example 2: Marking Effects

[0034] The instrument used for sample analysis is UPLC-ESI-LTQ-Orbitrap MS mass spectrometry. The mass spectrometry system is an LTQ / Orbitrap XL ETD mass spectrometer from ThermoFisher (Waltham, MA, USA) equipped with an ESI ion source. Data acquisition and analysis software is Thermo Xcalibur 2.1Software version. The liquid phase system is Dionex Ultimate3000RSLC chromatograph (Thermo Scientific, Sunnyvale, CA, USA), equipped with LPG-3400A quaternary gradient pump with built-in online degasser, WPS-3000SL autosampler, and TCC-3000 column thermostat. The type of chromatographic column is Waters ACQUITYUPLC BEH C18 (2.1×100mm, 1.7μm), and the temperature of chromatographic column is 40°C. 0.1% formic acid aqueous solution (phase A) and ACN (phase B) were used as the mobile phase for chromatographic analysis, and the chromatographic gradient was: 0-5min 10%B, 5-42min 10%-90%B, 45-58min90%B, 58- 60 min 10% B at a flow rate of 0.4 mL / min.

...

Embodiment 3

[0042] Example 3: Comparison with reported labeling effects of reagents

[0043] In order to further evaluate the labeling effect of MPEA, we selected two other derivatization reagents with higher sensitivity reported in the literature for comparison, namely: N, N-dimethylethylenediamine (DMED) and N-4-formazan Aminobenzylaniline (4-AMBA). The experimental results are presented in the form of a heatmap as Figure 4 As shown, the darker the color, the stronger the mass spectrometry signal, and the better the effect of the labeled reagent. The results showed that the labeling effect of MPEA on various carboxyl compounds was significantly better than that of DMED and 4-AMBA.

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Abstract

The invention discloses application of N-methyl phenylethylamine (MPEA) and an isotope reagent (d3-MPEA) thereof in carboxyl compound detection. MPEA and d3-MPEA are used as labeling reagents, and theliquid chromatography-mass spectrometry technology is combined to detect carboxyl compounds in a biological sample. The reagent is high in universality and can be used for labeling short-chain fattyacid, medium-chain and long-chain fatty acids, polycarboxylic acid and amino acid at the same time. After the carboxylic acid is labeled by MPEA, sensitivity can be improved by 1-2 orders of magnitudes, the labeling effect is obviously superior to that of the reported labeling reagent, and the analysis flux is greatly improved.

Description

technical field [0001] The invention relates to the application of N-methylphenylethylamine (MPEA) and its isotopes in the detection of carboxyl compounds, in particular to the development and use of a pair of isotope reagents that can label various types of carboxyl compounds, and belongs to the field of organic chemistry and analytical chemistry . Background technique [0002] Carboxyl metabolites are an important class of metabolites in living organisms, and there are many types, such as short-chain fatty acids, medium and long-chain fatty acids, polycarboxylic acids and amino acids. Carboxyl metabolites not only contain many types of functional groups, but also have large differences in chemical properties, and their biological activities are also greatly different. At the same time, most of these carboxyl metabolites come from different metabolic pathways and are related to each other. More and more reports point out that carboxyl metabolites are closely related to th...

Claims

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Application Information

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IPC IPC(8): G01N30/02G01N30/06G01N30/12G01N30/72G01N30/88
CPCG01N30/02G01N30/06G01N30/12G01N30/72G01N30/88G01N2030/062G01N2030/067G01N2030/126G01N2030/8813G01N2030/884
Inventor 冯钰锜郑杰郑书剑
Owner WUHAN UNIV
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