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Isotope derivatization reagent for labeling amino/phenolic hydroxyl and synthesis method thereof

A technology for derivatization reagents and synthesis methods, which is applied in the fields of organic chemistry, measuring devices, instruments, etc., can solve the problems of low commercialization degree and high price of isotope internal standard reagents, and achieve the effect of saving costs, improving efficiency and accuracy

Inactive Publication Date: 2019-01-01
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the isotope internal standard reagent is limited by its high price and low degree of commercialization, and is usually only suitable for the situation where there are few target analytes.

Method used

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  • Isotope derivatization reagent for labeling amino/phenolic hydroxyl and synthesis method thereof
  • Isotope derivatization reagent for labeling amino/phenolic hydroxyl and synthesis method thereof
  • Isotope derivatization reagent for labeling amino/phenolic hydroxyl and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment one (corresponding reagent series one)

[0031] Select p-aminophenylacetic acid, NaBH3CN and CH 2 O is raw material, and concrete steps are:

[0032] a) Use a 1.5mL centrifuge tube to directly weigh 10mg (0.066mmol) p-aminophenylacetic acid;

[0033] b) Use 500 μL of ultrapure water to dissolve p-aminophenylacetic acid, which can be dissolved by shaking or ultrasound;

[0034] c) Add 7.4% CH2 O 100μL, mix well during the shaking period of 10s;

[0035] d) Add 0.6mol / L catalyst NaBH 3 CN 150μL, mix well during shaking for 10s;

[0036] e) Use 0.5% formic acid (FA) to control the pH of the solution to 5, and dilute to 1 mL with ultrapure water;

[0037] f) React for 1 h at room temperature under the condition of 500 rpm. Through above-mentioned six steps operation, can obtain p-dimethylaminophenylacetic acid altogether (reaction equation is as follows);

[0038]

[0039] g) Transfer the dimethylation reaction product of the first step into a clean 25m...

Embodiment 2

[0046] Embodiment two (corresponding reagent series one)

[0047] Use p-aminophenylbutyric acid, NaBH 3 CN and CD 2 O is a raw material, and its concrete steps are:

[0048] a) Use a 1.5mL centrifuge tube to directly weigh 10mg p-aminobenzenebutyric acid;

[0049] b) Use 500 μL of ultra-pure water to dissolve p-aminophenylbutyric acid, which can be dissolved by shaking or ultrasound;

[0050] c) Add 20% CH 2 O 30μL, shake well for 10s;

[0051] d) Add 0.6mol / L catalyst NaBH 3 CN 150μL, mix well during shaking for 10s;

[0052] e) Use 0.5% formic acid (FA) to control the pH of the solution to 6, and dilute to 1 mL with ultrapure water;

[0053] f) React for 1 h at room temperature under the condition of 500 rpm. Through above-mentioned six steps operation (reaction equation is as follows);

[0054]

[0055] g) Transfer the dimethylation reaction product of the first step into a clean 25mL round bottom flask, and directly use a rotary evaporator to remove water (rota...

Embodiment 3

[0062] Embodiment three (corresponding reagent series one)

[0063] Select 4-(2-aminoethyl)benzoic acid, NaBD 3 CN and CH 2 O is a raw material, and its concrete steps are:

[0064] a) Use a 1.5mL centrifuge tube to directly weigh 10mg of 4-(2-aminoethyl)benzoic acid;

[0065] b) Use 500 μL of ultrapure water to dissolve 4-(2-aminoethyl)benzoic acid, which can be dissolved by shaking or ultrasound;

[0066] c) Add 7.4% CH 2 O 140μL, mixed well during the shaking period of 10s;

[0067] d) Add 0.6mol / L catalyst NaBD 3 CN 160μL, mix well during the shaking period of 10s;

[0068] e) Use 0.5% formic acid (FA) to control the pH of the solution to 6, and dilute to 1 mL with ultrapure water;

[0069] f) React for 1 h at room temperature under the condition of 500 rpm. Through above-mentioned six steps operation (reaction equation is as follows);

[0070]

[0071] g) Transfer the dimethylation reaction product of the first step into a clean 25mL round bottom flask, and di...

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Abstract

The invention provides an isotope derivatization reagent for labeling amino / phenolic hydroxyl and a synthesis method thereof and belongs to the field of chemical synthesis. A homologous compound of p-aminophenylacetic acid containing amino, a benzene ring and carboxyl in a structure or a homologous compound of 4-(2-aminoethyl)benzoic acid is used as a raw material; and the amino is dimethylated and then the carboxyl in the product is subjected to esterification by adopting N-hydroxysuccinimide to obtain the isotope derivatization reagent. The isotope derivatization reagent has structure characteristics that one part of the isotope derivatization reagent is succinimidyl ester and the other part of the isotope derivatization reagent is dimethyl substituted tertiary amino; the succinimidyl ester is connected to dimethylamino through a carbon chain and a benzene ring; and the number of carbon atoms on the benzene ring and the carbon chain which is connected to the amino is 0 to 6. According to the isotope derivatization reagent provided by the invention, different D substituted or <13>C substituted formaldehyde, or H or D substituted sodium cyanoborohydride are selected and a reactionroute is adjusted to obtain a series of isotope labeled reagents which can efficiently react with amino or phenolic hydroxyl and have different isotope substitutions. A starting raw material is changed, and the isotope labeled reagents with similar functions can be prepared through the method.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and relates to a group of isotope labeling reagents used for labeling a series of compounds with amino groups or phenolic hydroxyl groups and a synthesis method thereof. With the help of the labeling reagents, the target substance in the sample is labeled, and the liquid phase Chromatography-mass spectrometry (LC-MS) technology can achieve efficient and accurate quantitative analysis of the derivatized products of these two types of substances and the separation of isomers. Moreover, the reagent can introduce a benzene ring to increase the ultraviolet absorption intensity after labeling, which in turn helps to reduce the detection line of the target object by the ultraviolet spectrophotometer and HPLC-UV. Background technique [0002] Mass spectrometry (mass spectrometry) plays an important role in modern analysis technology, and the quantitative method based on mass spectrometry is also develop...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/46G01N30/02G01N30/74
CPCC07D207/46G01N30/02G01N30/74G01N2030/027
Inventor 吴明火景思源张娜珍周豪
Owner DALIAN UNIV OF TECH
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