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Amino functional group chiral compound resolution mark band fluorescence derivatizing agent

A chiral compound, fluorescence derivatization technology, applied in the field of biological analysis, can solve the problem of incomplete chiral resolution, and achieve the effect of reliable fluorescent chiral derivatization reagents

Active Publication Date: 2017-05-31
YANBIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these fluorescent derivatization reagents have not yet achieved complete chiral resolution for 19 chiral amino acids out of 20 amino acids.

Method used

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  • Amino functional group chiral compound resolution mark band fluorescence derivatizing agent
  • Amino functional group chiral compound resolution mark band fluorescence derivatizing agent
  • Amino functional group chiral compound resolution mark band fluorescence derivatizing agent

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Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0018] Synthesis of DBD-M-Pro:

[0019] 100 mg of DBD-F is dissolved in 10 mL of acetonitrile solution, 54 mg of M-L-Pro is dissolved in 10 mL of 0.25 M Na 2 CO 3 In the solution, the two solutions were mixed and reacted on a thermostatic magnetic stirrer at 30°C for 1 hour, and the solvent was evaporated under reduced pressure. The obtained residue was redissolved in 20 mL of water, and then the same volume of ethyl acetate was added. After fully standing still, the ethyl acetate layer was discarded, and the pH of the aqueous layer was adjusted to 1-2 with 2.0 mol / L HCl. Then, the same amount of ethyl acetate was added for extraction, and the extraction was repeated three times. The combined ethyl acetate layer was dried over anhydrous sodium sulfate, filtered, and evaporated to dryness under reduced pressure to obtain 78.6 mg of yellow powder. LC-ESI-TOF-MS spectral data, (m / z): 355.06 [M+H] + , t R =6.23 min; 1 H-NMR (300 MHz, CDCl 3 ) δ7.89 (t, J = 14.2 Hz, 1H), 6.00 (d, J ...

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Abstract

The invention relates to an amino functional group chiral compound resolution mark band fluorescence derivatizing agent, in particular to a DBD-trans-2-methyl-L-proline (DBD-M-Pro) agent and a DBD-(2-succinimidoxy)-trans-2-methyl-L-proline (DBD-M-Pro) agent. The two agents contain benzofurazan as a fluorescence functional group and a chiral center structure, can carry out fluorescence marking on an amino functional group chiral compound and establishes an analysis method with high sensitivity and high selectivity in amino functional group chiral compound resolution by utilizing a liquid chromatography-fluorescence detection (LC-FL) technology. Since containing the fluorescence functional group self, the agent can remarkably improve the detection sensitivity in a fluorescence detector, can also carry out chiral resolution on the amino functional group chiral compound in reversed phase chromatography and supplies a novel high-sensitivity fluorescence chiral derivatizing agent for studying resolution of an amino functional group chiral metabolite and screening various disease chiral biomarkers.

Description

Technical field [0001] The present invention relates to the analysis of chiral metabolites containing amino functional groups in the field of biological analysis, in particular to a novel high-sensitivity fluorescent derivatization reagent for chiral resolution of chiral compounds with amino functional groups. Background technique [0002] Chirality is a basic feature of biological systems, especially in the field of pharmacy. In many cases, the biological activities of two isomer drugs, such as pharmacodynamics and pharmacokinetics, sometimes have significant differences. Chirality is an important feature of many endogenous metabolites. In order to accurately screen the truly effective chiral biomarkers, liquid chromatography-fluorescence detection (LC-FL) technology is used to develop and establish a highly sensitive method for the separation and analysis of chiral metabolites. The elucidation of diagnosis and gene function, the safety evaluation of pharmaceutical ingredients...

Claims

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Application Information

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IPC IPC(8): G01N30/06G01N30/88G01N30/74
CPCG01N30/06G01N30/74G01N30/88
Inventor 闵俊哲黄媛娄喆
Owner YANBIAN UNIV
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