Amino functional group chiral compound resolution labeling with fluorescent derivatization reagent

A chiral compound, fluorescence derivatization technology, applied in the field of biological analysis, can solve the problem of not achieving complete chiral resolution, and achieve the effect of reliable fluorescent chiral derivatization reagents

Active Publication Date: 2019-05-14
YANBIAN UNIV
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  • Abstract
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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 labeling with fluorescent derivatization reagent
  • Amino functional group chiral compound resolution labeling with fluorescent derivatization reagent
  • Amino functional group chiral compound resolution labeling with fluorescent derivatization reagent

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Experimental program
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Embodiment Construction

[0018] Synthesis of DBD-M-Pro:

[0019] Dissolve DBD-F 100 mg in 10 mL of acetonitrile solution, M-L-Pro 54 mg in 10 mL of 0.25 M Na 2 CO 3 The two solutions were mixed, reacted at 30° C. for 1 hour on a constant temperature magnetic stirrer, and the solvent was distilled off under reduced pressure. The resulting residue was re-dissolved in 20 mL of water, and then the same volume of ethyl acetate was added. After sufficient static, 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, an equal amount of ethyl acetate was added for extraction, and the extraction was repeated three times. The combined ethyl acetate layers were 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 ) δ 7.89 (t, J = 14.2 Hz, 1H), 6.00 (d, J = 8.2 Hz, 1H), 4...

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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 invention relates to the analysis of chiral metabolites containing amino functional groups in the field of biological analysis, in particular to novel high-sensitivity fluorescent derivatization reagents for chiral resolution of chiral compounds with amino functional groups. Background technique [0002] Chirality is a fundamental feature of biological systems, especially in the field of pharmacy. In many cases, the biological activities of two isomeric drugs, such as potency and pharmacokinetics, sometimes differ significantly. Chirality is in turn an important feature of many endogenous metabolites. In order to accurately screen truly effective chiral biomarkers, liquid chromatography-fluorescence detection (LC-FL) technology is used to develop and establish a highly sensitive chiral metabolite separation and analysis method, which is useful for drug toxicity and mechanism research, disease It is of great significance for the elucidation of dia...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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