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Sugar chain relative quantitative isotope labeling mass spectrum derivatization reagent

A technology for quantitative isotopes and derivatization reagents, applied in the field of biological analysis, can solve the problems of difficult synthesis, difficulty in obtaining, expensive, etc., and achieve high selectivity.

Pending Publication Date: 2020-05-29
YANBIAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, sugar chain standard products are difficult to synthesize and expensive to obtain. Therefore, relative quantitative analysis of isotope labeling is mainly used at present.

Method used

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  • Sugar chain relative quantitative isotope labeling mass spectrum derivatization reagent
  • Sugar chain relative quantitative isotope labeling mass spectrum derivatization reagent
  • Sugar chain relative quantitative isotope labeling mass spectrum derivatization reagent

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Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0030] Synthesis of d0-DPBOC:

[0031] L-2-Thiazolidinone-4-carboxylic acid (L-2-Thiazolidinone-4-carboxylic-acid, OTZD), 100.0 mg dissolved in 2.0 mL N,N- Add 184.6 μL of triethylamine to dimethylformamide (DMF), slowly add 92.4 μL of benzoyl chloride (d0) dropwise under the condition of stirring in an ice bath, and stop the reaction after stirring in an ice bath for 2 h. Add 10 mL of water, adjust the pH value of the reaction solution with acid, add the same volume of ethyl acetate, and after fully standing still, discard the water layer. Then add an equal volume of ethyl acetate, repeat the extraction 3 times, combine the ethyl acetate layers and dry over anhydrous sodium sulfate, filter with suction, add silica gel and spin dry, and separate by column chromatography to obtain 98.3 mg of white solid with a yield of about It was 59.17%.

[0032] d0-BZC-OTZD 92.5 mg, add 8 mL of dichloromethane (DCM) to dissolve, then add 52.2 mg of NHS, dicyclohexylcarbodiimide (DCC) 93.6...

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Abstract

The invention discloses a sugar chain relative quantitative isotope labeling mass spectrum derivatization reagent, and particularly relates to a d0-DPBOC reagent and a d5-DPBOC reagent. The structureof the reagent contains an N-hydroxysuccinimide activated carboxyl structure so that a sugar chain of glycoprotein digested by streptavidin E can be labeled under an alkaline condition, and the retention of the labeled sugar chain in a reversed-phase chromatographic column is enhanced. Besides, the reagent contains a d0 / d5 stable light and heavy isotope benzoyl (d0 / d5-Benzoyl acyl) structure, relative quantitative analysis of the sugar chain can be carried out based on an isotope ratio (d0 / d5) by utilizing a liquid chromatography-mass spectrometry technology, and a sugar chain standard substance is not needed. A novel high-sensitivity isotope mass spectrum derivatization reagent is provided for research of differential glycomics and screening of new biomarkers of disease carbohydrate chains.

Description

technical field [0001] The invention relates to the relative quantitative analysis of sugar chains in glycoproteins in the field of biological analysis, in particular to high-sensitivity and high-selectivity isotope-labeled mass spectrometry derivatization reagents for screening disease sugar chain markers. Background technique [0002] Glycosylation is one of the most prevalent and complex forms of protein post-translational modification. More than 70% of the proteins in the human body are glycosylated, and the complex diversity and micro-heterogeneity of their structures make the sugar chains have more branched structures, connection methods and spatial conformations. Changes in the structure and expression of sugar chains are closely related to diseases such as human immunity, inflammation, tumors and metabolism. But at this stage, it is still impossible to study the detailed structural information of sugar chains at the level of complete glycoproteins. Therefore, most o...

Claims

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Application Information

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IPC IPC(8): G01N30/89G01N30/06G01N30/14G01N30/12G01N30/72G01N30/88C07D417/12
CPCG01N30/89G01N30/06G01N30/14G01N30/12G01N30/72G01N30/88C07D417/12G01N2030/067G01N2030/062G01N2030/126G01N2030/8868
Inventor 闵俊哲罗苗石清肖淑云许春燕
Owner YANBIAN UNIV
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