Stable isotope amino compound labeling reagent as well as synthesis method and application thereof

An amino compound and stable isotope technology, applied in the direction of isotope introduction into organic compounds, organic chemistry methods, chemical instruments and methods, etc., can solve the problems of poor labeling accuracy and sensitivity, difficult to obtain isotope products, complex synthesis of labeling reagents, etc. The effect of high labeling yield, simple detection of amino compounds, and fast labeling reaction rate

Inactive Publication Date: 2021-09-17
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the current chemical labeling methods have some defects more or less, such as slow labeling reaction rate, low labeling yield, weak labeling product signal, poor labeling accuracy and sensitivity, etc., and the synthesis of many labeling reagents is complicated, The corresponding isotopic products are not readily available, thus limiting their widespread use

Method used

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  • Stable isotope amino compound labeling reagent as well as synthesis method and application thereof
  • Stable isotope amino compound labeling reagent as well as synthesis method and application thereof
  • Stable isotope amino compound labeling reagent as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

no. 1 example

[0050] Refer to the following route 1 (wherein, X=D) to carry out the heavy-duty labeling reagent [d 4 The synthesis of ]-2-(9-acridone) ethyl chloroformate comprises the steps:

[0051] 1. Intermediate I: [d 5 Preparation of ]-N-phenylanthranilic acid:

[0052] Add 20g of anthranilic acid, 1g of copper powder and 10g of potassium carbonate to a 250mL three-necked flask, then add 150mL of dimethyl sulfoxide as a solvent, stir and mix evenly, then add 15g of deuterated bromobenzene- d 5 , and then reacted with stirring in an oil bath at 150° C. for 5 hours (anthranilic acid and deuterated bromobenzene-d 5 undergo a substitution reaction).

[0053] After the reaction, filter, remove excess copper powder and potassium carbonate, and collect the filtrate. Pour the filtrate into 200mL of clear water, adjust the pH value to 5 with concentrated hydrochloric acid, stir thoroughly, filter after the solid product is completely precipitated, put the obtained solid product in an oven...

no. 2 example

[0072] The reference application number is] CN202010117911.8, the synthetic route in the Chinese patent literature titled "Acridone Fluorescamine Compound Labeling Reagent and Its Synthetic Method and Application", to prepare light labeling reagent [d 0 ]-2-(9-acridone) ethyl chloroformate, the target product B.

[0073] The target product B synthesized in this embodiment is characterized, and its NMR 1 H NMR spectrum such as figure 2 Shown:

[0074] 1 HNMR (500MHz, DMSO) δ8.36 (dd, J = 8.0, 1.5Hz, 2H), 7.92 (d, J = 8.8Hz, 2H), 7.82 (ddd, J = 8.7, 7.0, 1.6Hz, 2H), 7.33(t, J=7.4Hz, 2H), 4.61(t, J=6.3Hz, 2H), 3.90(t, J=6.3Hz, 2H).

[0075] 13 CNMR (126MHz, DMSO) δ176.96, 142.44, 142.32, 134.39, 126.99, 122.02, 121.65, 116.88, 58.59, 48.03

[0076] Found: Found: C63.79, H3.99Cl11.79, N4.65, O15.95; Calculated: C63.69, H4.01Cl11.75, N4.64, O15.91.

[0077] MS:m / z:[M+H] + = 302.1.

[0078] It can be seen that the target product B was successfully synthesized in this examp...

no. 3 example

[0081] A method for detecting the concentration of biogenic amine in an analyte using a stable isotope amino compound labeling reagent, that is: using the heavy-duty labeling reagent and light-duty labeling reagent prepared respectively in the first embodiment and the second embodiment to test biogenic amine, details as follows:

[0082] The first step: prepare borax / boric acid buffer solution with pH=9.5; the preparation concentration is 1×10 -6 mol / L biogenic amine standard acetonitrile solution; the prepared concentration is 1×10 -4 mol / L[d 0 ]-2-(9-acridone) ethyl chloroformate in acetonitrile solution as a light labeling reagent solution; the preparation concentration is 1×10 -4 mol / L[d 4 ]-2-(9-acridone) ethyl chloroformate in acetonitrile solution as a heavy-duty labeling reagent solution for subsequent use.

[0083] Step 2: sequentially add 200 μL of the borax / boric acid buffer solution, 100 μL of biogenic amine standard solution and 50 μL of light labeling reagent...

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Abstract

The invention relates to the technical field of stable isotope labeling, in particular to a stable isotope amino compound labeling reagent and a synthesis method and application thereof. The chemical structural formula of the labeling reagent is as shown in formula 1 in the specification, wherein in the formula 1, X is D, and the labeling reagent is [d4]-2-(9-acridone)-ethyl chloroformate; and R is any one of F, Cl, Br, I and other elements, and n is equal to 2 or 3. The isotope labeling reagent provided by the invention takes acridone as a parent ring and an isotope labeling group and chloroformate as a reaction group, can selectively label an amino compound, and has the advantages of simple and convenient synthesis method, high labeling reaction rate, strong signal of a labeled product, high labeling yield and high amino selectivity; and the accuracy and the sensitivity of mass spectrometric detection of the amino compound are enhanced.

Description

technical field [0001] The invention relates to the technical field of stable isotope labeling, in particular to a stable isotope amino compound labeling reagent and its synthesis method and application. Background technique [0002] The information disclosed in the Background of the Invention is only intended to increase the understanding of the general background of the invention, and is not necessarily to be taken as an acknowledgment or any form of suggestion that the information constitutes the prior art that is already known to those skilled in the art. [0003] High-performance liquid chromatography-mass spectrometry (HPLC-MS / MS) is widely used in research fields such as life analysis, environmental detection, and food evaluation due to its high sensitivity and high selectivity. Targeted and semi-targeted analytes in samples can be selectively monitored using the selected reaction monitoring (SRM) or multi-stage reaction ion monitoring (MRM) mode of HPLC-MS / MS. Howev...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B59/00C07D219/06G01N30/02G01N30/06G01N30/30G01N30/32G01N30/34G01N30/72
CPCC07B59/002C07D219/06G01N30/02G01N30/06G01N30/30G01N30/32G01N30/34G01N30/72C07B2200/05G01N2030/324
Inventor 尤进茂谭江坤王博李赞孙志伟纪仲胤
Owner QUFU NORMAL UNIV
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