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A protein chemical cross-linking agent and its preparation method and application

A chemical cross-linking agent, protein technology, applied in the field of protein and its function research, can solve problems such as poor stability, low cross-linking efficiency, and reduced water-solubility of cross-linking agents

Active Publication Date: 2020-11-06
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, simply mechanically piecing these functional groups together sometimes cannot realize their own value, and improper accumulation will bring negative effects, resulting in problems such as reduced water solubility of the crosslinking agent, low crosslinking efficiency, and poor stability.
Therefore, how to organically fuse these functional groups together so that they can exert their own functions and become a chemical cross-linking agent that can solve the analysis of complex biological samples is still a great challenge.

Method used

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  • A protein chemical cross-linking agent and its preparation method and application
  • A protein chemical cross-linking agent and its preparation method and application
  • A protein chemical cross-linking agent and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] The present embodiment adopts the step (1) of the above-mentioned method, carries out the substitution reaction with dibromoethane and p-hydroxyacetophenone as raw materials, and obtains the following product:

[0062]

[0063] The characterization information is as follows:

[0064] White solid; 226mg, yield 76% (calculated with 1mmol dibromoethane and 3mmol p-hydroxyacetophenone as raw materials);

[0065] m.p.167-169°C;

[0066] IR (neat) 1666, 1602, 1253cm -1;

[0067] 1 H NMR (400MHz, CDCl 3 )δ7.95(d, J=8.8Hz, 4H), 6.99(d, J=8.8Hz, 4H), 4.41(s, 4H), 2.56(s, 6H);

[0068] 13 C NMR (100MHz CDCl 3 )δ26.5, 66.6, 114.4, 130.8, 130.9, 162.5, 196.9;

[0069] MS(ESI)m / z 299(M+H) + ;

[0070] HRMS(ESI)m / z C 18 h 19 o 4 (M+H) + The theoretical value is: 299.12779, and the measured value is 299.12764.

[0071] In this example, on the basis of the obtained pre-ArGO-1, the following product is obtained through the reaction of step (2):

[0072]

[0073] Th...

Embodiment 2

[0084] The present embodiment adopts the step (1) of the above-mentioned method, carries out the substitution reaction with diiodoethyl ether and p-hydroxyacetophenone as raw materials, and obtains the following product:

[0085]

[0086] The characterization information is as follows:

[0087] White solid; 278mg, yield 81% (calculated using 1mmol diiodoethyl ether and 3mmol p-hydroxyacetophenone as raw materials);

[0088] m.p.113-115°C;

[0089] IR (neat) 1676, 1601, 1257, 1065cm -1 ;

[0090] 1 H NMR (400MHz, CDCl 3 )δ7.91(d, J=8.8Hz, 4H), 6.93(d, J=8.8Hz, 4H), 4.21(t, J=4.6Hz, 4H), 3.95(t, J=4.7Hz, 4H) ,2.54(s,6H);

[0091] 13 C NMR (100MHz CDCl 3 )δ26.5, 67.7, 69.9, 114.4, 130.6, 130.7, 162.7, 196.9;

[0092] MS(ESI)m / z 343(M+H) + ;

[0093] HRMS(ESI)m / z C 20 h 23 o 5 (M+H) + The theoretical value is 343.15400, and the measured value is 343.15400.

[0094] In this example, on the basis of the obtained pre-ArGO-2, after step (2) reaction, the following p...

Embodiment 3

[0107] In this example, step (1) of the above method is adopted, and 1,2-bis(2-iodoethoxy)ethane and p-hydroxyacetophenone are used as raw materials for substitution reaction to obtain the following product:

[0108]

[0109] The characterization information is as follows:

[0110] White solid; 316mg, yield 82% (calculated using 1mmol 1,2-bis(2-iodoethoxy)ethane and 3 mmol p-hydroxyacetophenone as raw materials);

[0111] m.p.173-175℃;

[0112] IR (neat) 1673, 1600, 1255cm -1 ;

[0113] 1 H NMR (400MHz, CDCl 3 )δ7.91(d, J=8.8Hz, 4H), 6.93(d, J=8.8Hz, 4H), 4.18(t, J=4.7Hz, 4H), 3.89(t, J=4.7Hz, 4H) ,3.77(s,4H),2.54(s,6H);

[0114] 13 C NMR (100MHz CDCl 3 )δ26.5, 67.7, 69.7, 71.1, 114.4, 130.6, 130.7, 162.8, 196.9;

[0115] MS(ESI)m / z 387(M+H) + ,409(M+Na) + ;

[0116] HRMS(ESI)m / z C 20 h 23 o 6 (M+H) + The theoretical value is 387.18022, and the measured value is 387.18094.

[0117] In this example, on the basis of the obtained pre-ArGO-3, the following prod...

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Abstract

The invention relates to a chemical cross-linking agent for proteins and a preparation method thereof. The multifunctional cross-linking agent provided by the invention has excellent water-solubilityand stability, and high cross-linking efficiency, especially high cross-linking efficiency to arginine, and the multifunctional cross-linking agent is the first extensively-used specific cross-linkingagent for arginine. It is proved that the cross-linking agent has arginine selectivity; and cross-linking reactions of the multifunctional cross-linking agent with proteins of eight modes and oligomeric yeast protein compounds prove the validity of conjugation between the cross-linking agent and arginine. Combined chemical cross-linking and mass spectrometric technology is an effective and rapidly developing technology in structural chemistry and can be effectively applied to analysis of large active protein compounds without strict purification. Due to diversified structural characteristicsof the cross-linking agent, the cross-linking agent presents complementary reactivity, and arginine residues cross-linkable with the cross-linking agent are all specific.

Description

technical field [0001] The invention relates to the field of protein and its function research, in particular to a protein chemical cross-linking agent and a preparation method thereof. Background technique [0002] As the material basis of life and the main bearer of life activities, the study of protein functions is of great significance to the understanding of life activities. With the completion of the Human Genome Project, the number of proteins identified has increased dramatically over the past decade. However, the physiological functions of many newly discovered proteins are still unclear, and the three-dimensional structure of proteins and protein-protein interactions are closely related to the study of protein functions. The resolution of traditional protein structure analysis methods such as X-ray crystallography and nuclear magnetic resonance spectroscopy can reach the atomic level. However, both of these methods require a large amount of protein, and it is ver...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/84C07C45/64C07C235/84C07C231/12G01N33/68
Inventor 雷晓光亚历山大·琼斯董梦秋曹勇谭惠
Owner PEKING UNIV
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