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Stable isotope mercapto compound labeling reagent and its synthesis method and application

A technology of thiol compounds and stable isotopes, applied in organic chemistry methods, organic chemistry, instruments, etc., can solve the problems of poor labeling accuracy and sensitivity, difficult access to labeling reagents, and weak signals of labeled products, achieving high sensitivity and selection The effect of high accuracy, fast labeling reaction rate, enhanced accuracy and sensitivity

Inactive Publication Date: 2019-02-22
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, all the chemical labeling methods so far have some defects, such as slow labeling reaction rate, weak labeling product signal, poor labeling accuracy and sensitivity, etc., and many labeling reagents are not easy to obtain, thus limiting their widespread use

Method used

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  • Stable isotope mercapto compound labeling reagent and its synthesis method and application
  • Stable isotope mercapto compound labeling reagent and its synthesis method and application
  • Stable isotope mercapto compound labeling reagent and its synthesis method and application

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Experimental program
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Effect test

Embodiment 1

[0034] Such as figure 1 As shown, the synthesis of the stable isotope mercapto compound labeling of the present invention has 6 steps in total, and the synthetic route is as follows figure 1 , the heavy-duty labeling reagent uses [d5]-bromobenzene as a raw material, and the synthesis operation of the heavy-duty labeling reagent is as follows:

[0035] 1. Preparation of intermediate Ⅰ[d5]-2-anilinobenzoic acid

[0036] Add 22g of anthranilic acid, 20g of [d5]-bromobenzene, 10g of potassium carbonate and 0.5g of copper powder into a 250mL three-neck flask, add 150mL of nitrobenzene as a solvent, heat and reflux on a heating mantle, and stir for 3 hours; the reaction is complete Afterwards, the solvent was distilled off with steam, and the mixed reaction solution was poured into 200 ml of water, neutralized with concentrated hydrochloric acid to a pH value of 5-6, stirred thoroughly, and the precipitated solid was filtered and dried to obtain intermediate I as a gray powder . ...

Embodiment 2

[0056] Prepare a PBS buffer solution with a pH of 7.4 and a concentration of 0.01mol / L; prepare a concentration of 1×10 -4 Acetonitrile solution of [d0]-AENM and [d4]-AENM in mol / L; the preparation concentration is 1×10 -6 A series of thiol standards in mol / L (3-mercapto-hexanol, hexanethiol, furfuryl mercaptan, 2-methyl-3-furyl mercaptan, phenethanethiol, 3-mercapto-acetic acid-hexane ester, 4-methyl-4-mercapto-2-pentanone) in acetonitrile.

[0057] Add 50 μL of PBS buffer solution, 100 μL of thiol standard solution and 50 μL of acetonitrile solution of light-duty labeling reagent [d0]-AENM to a 2 mL ampoule in sequence, and react in a water bath at 40°C for 10 minutes. At the same time, under the same conditions, the real sample of wine after column purification was labeled with the heavy reagent [d4]-AENM. After the reaction was completed, they were mixed at a volume ratio of 1:1, and then analyzed by HPLC-MS / MS.

[0058] The peak area of ​​the light derivative obtained ...

Embodiment 3

[0061] Quantification of mercaptans was performed using Agilent 1290 ultra-high performance liquid chromatography, 6460 triple quadrupole tandem mass spectrometer, equipped with electrospray ionization source (ESI). Chromatographic conditions: mobile phase A is 5% acetonitrile + 95% water, mobile phase B is 100% acetonitrile, and 0.1% formic acid is added to the mobile phase to enhance the ionization efficiency of the analyte; use gradient elution, set the mobile phase B. The initial gradient is 30%, which becomes 100% after 10 minutes and is maintained for 5 minutes; the injection volume is 1 μL, and the flow rate is 0.2 mL / min. Mass spectrometry conditions: ESI positive ion mode, drying gas temperature 300°C, flow rate 10L / min, atomization pressure 40psi, sheath gas temperature 250°C, flow rate 8L / min, capillary voltage 3.5KV. Collision voltage (Fragmentor) and fragmentation energy (CE) parameters are as follows:

[0062]

[0063] Derivatives all show strong [M+H] + Sig...

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Abstract

The invention relates to the technical field of organic small molecule isotope labeling, in particular to a stable isotope mercapto compound labeling reagent, a synthesis method and application thereof. The isotope labeling reagent is [d0] / [D4]-acridone-10-ethyl-N-maleimide. The reagent adopts acridone as the isotope group and takes maleimide as the reaction group. The synthesis method includes: taking [d0] / [D5]-bromobenzene as the raw material, and carrying out two-step condensation reaction, hydroxylation reaction, helogenation reaction, Gabriel reaction and acylation reaction, thus obtaining the reagent. The stable isotope deuterium label obtained by the invention is subjected to separation and purification, then the isotope labeling position is table, the chemical purity is up to 99.0% or more, and the isotope abundance is up to 99.0% or more. The reagent can selectively label mercapto compounds, and has the advantages of fast labeling reaction rate, high labeling yield and high mercapto selectivity, etc.

Description

technical field [0001] The invention relates to the technical field of isotope labeling of small organic molecules, in particular to a stable isotope mercapto compound labeling reagent and its synthesis method and application. Background technique [0002] High-performance liquid chromatography-tandem mass spectrometry (HPLC-MS / MS) is widely used in research fields such as life analysis, environmental analysis, and food analysis due to its high sensitivity and high selectivity. The selected reaction monitoring (SRM) or multi-stage reaction ion monitoring (MRM) mode of HPLC-MS / MS can selectively monitor the specified analyte in the sample, which can effectively reduce the influence of noise and improve the sensitivity of detection. However, due to the problem of signal attenuation or enhanced matrix effect caused by the sample matrix or co-eluting substances, the analytical performance of HPLC-MS / MS is greatly reduced, which is described in detail in Journal of Chromatography...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/06G01N30/02
CPCC07B2200/05C07D401/06G01N30/02
Inventor 尤进茂吕政贤路帅敏窦昆孙志伟李国梁
Owner QUFU NORMAL UNIV
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