A kind of universal low-cost quaternary ammonium salt sugar chain isotope labeling reagent and synthesis method

A technology for sugar chains and compounds, which is applied in the field of universal low-cost quaternary ammonium salt sugar chain isotope labeling reagents and synthesis, can solve the problems of difficult wide application, expensive synthetic raw materials, and poor economical use, so as to improve sensitivity and development costs Low, good resolution effect

Active Publication Date: 2022-08-05
NORTHWEST UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, d 7 -HIQB is difficult to achieve wide application due to the high price of synthetic raw materials and poor economical use

Method used

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  • A kind of universal low-cost quaternary ammonium salt sugar chain isotope labeling reagent and synthesis method
  • A kind of universal low-cost quaternary ammonium salt sugar chain isotope labeling reagent and synthesis method
  • A kind of universal low-cost quaternary ammonium salt sugar chain isotope labeling reagent and synthesis method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] A method for synthesizing a general low-cost quaternary ammonium salt sugar chain isotope labeling reagent, the specific steps are as follows:

[0059] S1, place a 25 mL round-bottomed flask containing 10 mL of methanol on an electronic balance, weigh 1.0 g of deuterated 4-methylpyridine into the round-bottomed flask, and then weigh 2.0 g of ethyl bromoacetate into the round-bottomed flask. Set up a condensation reflux device, and stir and reflux at 70 °C for 12 h;

[0060] S2, place the obtained mixture in an ice bath, add 1.2 mL of 80% hydrazine hydrate dropwise with stirring, and control the flow rate to complete the dropwise addition within 30 min, then seal the round-bottomed flask, and continue to stir the reaction in the ice bath for 2 h;

[0061] S3, after the reaction is completed, use a rotary evaporator to concentrate the reaction solution to an oily state, then add 10 mL of dehydrated ethanol pre-cooled at -20 °C in advance, stir in an ice bath for 30 min, a...

Embodiment 2

[0065] The mass spectrometry detection sensitivity evaluation of a sugar chain derivative of a general low-cost quaternary ammonium salt sugar chain isotope labeling reagent, the specific operation steps are as follows:

[0066] S1, weigh 9.9 mg of maltohexaose and 11.34 mg of β-cyclodextrin, respectively prepare an aqueous solution of 1 mmol / L, get the solution of maltohexaose and β-cyclodextrin, mix them in a molar ratio of 5:1, and the resulting mixture solution It was used for analysis by MALDI-TOF MS.

[0067] S2, 24.5 mg of HMP was weighed and dissolved in 1 mL of solvent (methanol:water:glacial acetic acid=6:3:1) to prepare a 0.1M HMP reaction solution.

[0068]The mixture samples in S3 and S1 were concentrated and dried by centrifugation, added 25uL of HMP reaction solution, reacted in a 70°C water bath for 1h, centrifuged and concentrated to remove the solvent, and then dissolved in 1mL of ultrapure water for MALDI-TOF MS detection.

Embodiment 3

[0076] Quantitative linear range and quantitative stability investigation of a general low-cost quaternary ammonium salt sugar chain isotope labeling reagent, the used sugar chain standard product is maltodextrin, and the specific steps are as follows:

[0077] S1, 1 mg of maltodextrin is weighed and dissolved in 0.5 mL of ultrapure water to prepare a sugar chain standard solution.

[0078] S2, weigh 24.5mg HMP and dissolve it in 1mL solvent (methanol:water:glacial acetic acid=6:3:1) to prepare 0.1M d 0 -HMP reaction solution; weigh 31.5mg d 7 -HMP was dissolved in 1 mL of solvent (methanol:water:glacial acetic acid=6:3:1) to make 0.1M d 7 -HMP reaction solution.

[0079] S3, use a micro-injection needle to take 1uL of the sugar chain standard solution and add it to a 0.5mL centrifuge tube, prepare 2 copies in total, and then add 25uLd 0 -HMP reaction solution and d 7 The -HMP reaction solution was reacted in a water bath at 70°C for 1 h, then centrifuged, concentrated and...

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Abstract

The invention relates to the technical field of biological glycomic analysis, and discloses a general low-cost quaternary ammonium salt sugar chain isotope labeling reagent and a synthesis method, including a labeling reagent in the form of heavy isotope deuterated 7-4-methyl-1-( 2-hydrazino-2-oxoethyl)-pyridinium bromide and its corresponding labeling reagent in light isotopic form 4-methyl-1-(2-hydrazino-2-oxoethyl)-pyridinium bromide Onium; can be used for mass spectrometry high-sensitivity and high-accuracy relative quantitative analysis of bioreducing sugar chains of different molecular weight segments; the reagent provided by the invention can greatly improve the mass spectrometry detection sensitivity of sugar chains; it is suitable for small and large molecular weight reducing sugar chains at the same time Relative quantitative analysis of sugar chains by mass spectrometry; low cost of synthetic raw materials, overcoming the disadvantage of high cost of hydrazide-based quaternary ammonium salt stable isotope labeling reagents synthesized based on deuterated isoquinoline.

Description

technical field [0001] The invention relates to the technical field of biological sugar group analysis, in particular to a general low-cost quaternary ammonium salt sugar chain isotope labeling reagent and a synthesis method. Background technique [0002] Glycans are a class of important biomolecules that are widespread in various organisms, including polysaccharides, free oligosaccharides, and glycoconjugate sugar chains. These glycans play an important role in a variety of life activities. For example, some non-digestible plant polysaccharides and animal breast milk oligosaccharides can promote the proliferation of beneficial intestinal flora, thereby playing a series of physiological regulating effects. Glycoproteins are an important class of glycoconjugates with O-linked sugar chains on serine or threonine residues (-Ser / Thr-) and N-linked on asparagine residues (-Asn-) As biological information molecules, sugar chains play important functions in various biological proc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/127C07D213/20G01N27/62G01N27/626
CPCC07D213/20C07D213/127G01N27/62G01N27/626C07B2200/05
Inventor 王承健邹美义王仲孚黄琳娟
Owner NORTHWEST UNIV
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