Benzenesulphonyl fluoride, preparing method and application thereof

A technology for benzenesulfonyl fluoride compounds, which is applied to benzenesulfonyl fluoride compounds and the fields of preparation and application thereof, can solve the problems of loss of stereochemical information, insufficient detection sensitivity, erroneous detection results, etc., and achieves stable and stable derivatized products. High instrument response value and good repeatability

Inactive Publication Date: 2009-11-25
李寿椿
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 1) Some labeling reagents are not fully applicable to certain amino acids that make up human proteins, for example, for secondary amino acids, tryptophan, cysteine, proline, hydroxyproline
[0004] 2) After some labeling reagents react with the functional group of the chiral center of α-amino acid, they will produce mesization, resulting in the loss of part or all of the stereochemical information
In peptides can cause partial or total epimerization of chiral centers to lose biological activity
[0005] 3) Most of the existing labeling reagents are sensitive to humidity in the ai...

Method used

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  • Benzenesulphonyl fluoride, preparing method and application thereof
  • Benzenesulphonyl fluoride, preparing method and application thereof
  • Benzenesulphonyl fluoride, preparing method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0023] 4-Methoxybenzenesulfonyl fluoride CH 3 O-C 6 h 4 -SO 2 Synthesis of F:

[0024] Add 10.5 g of sodium fluoride, 4008 g of polyethylene glycol and 200 ml of acetonitrile into a 500 ml four-neck round bottom flask with a stirrer, a reflux condenser, a thermometer jack and a feed port. Stir on a 30°C water bath for 60 minutes until sodium fluoride particles of uniform size are observed. Then, a suspension of 200 ml of acetonitrile containing 20.6 g of 4-methoxybenzenesulfonyl chloride was added to the above-mentioned four-neck flask.

[0025] Stirring was continued at 30°C for 120 minutes before the reaction was stopped. Pour the fluorinated reactant suspension into a 1000ml beaker filled with 400ml of distilled water under stirring, and let it stand overnight.

[0026] The fluorinated product was filtered out on a Buchner funnel, washed with ethanol to remove acetonitrile, dried and weighed to obtain 14 g of crude product of 4-methoxybenzenesulfonyl fluoride. Recrys...

Embodiment 2

[0029] 2-Methoxy 4-methylbenzenesulfonyl fluoride 2-CH 3 O4-CH 3 -C 6 h 4 -SO 2 Synthesis of F:

[0030] Add 12.6 g of sodium fluoride, 6008 g of polyethylene glycol and 200 ml of acetonitrile into a 500 ml four-necked flask with a stirrer, a reflux condenser, a thermometer jack and an inlet. Stir on a 30°C water bath for 60 minutes until sodium fluoride particles of uniform size are observed. Then, a suspension of 200 ml of acetonitrile containing 22 g of 2-methoxyl 4-methylbenzenesulfonyl chloride was added to the above-mentioned four-neck flask.

[0031] Stirring was continued at 30°C for 120 minutes before the reaction was stopped. Pour the fluorinated reactant suspension into a 1000ml beaker filled with 400ml of distilled water under stirring, and let it stand overnight.

[0032] The fluorinated product was filtered out on a Buchner funnel, washed with ethanol to remove acetonitrile, dried and weighed to obtain 14.2 g of crude 2-methoxy 4-methylbenzenesulfonyl fluo...

Embodiment 3

[0046] Determination of secondary amino acids: proline, hydroxyproline, and N-ethylglycine using 4-methoxybenzenesulfonyl fluoride as a labeling reagent:

[0047] Instruments: High performance liquid chromatography from Waters, USA: 510 pump, U6k injector, 490E ultraviolet detector, reversed-phase C8 chromatographic column.

[0048] Reagents: proline, hydroxyproline, N-ethylglycine (Aldrich product);

[0049] 4-methoxybenzenesulfonyl fluoride (SINORO-9AS2, self-made) in the series of benzenesulfonyl fluoride compounds;

[0050] Mobile phase: Accurately weigh 6.8g of crystalline sodium acetate, add about 850ml of deionized aqueous solution, adjust the pH to 4.2 with 10% acetic acid solution, add deionized water to 1000ml, filter with suction, take 770ml of this solution, add 230ml of chromatographically pure acetonitrile and mix well , degassed for standby;

[0051] Methods: ① Accurately prepare 100 μl each of proline aqueous solution, hydroxyproline aqueous solution, N-ethyl...

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Abstract

The present invention relates to benzenesulphonyl fluoride, a preparing method and an application thereof. The invention relates to the compound with the general formula of (I), wherein R is alkyl, alkoxyl, acyl, carboxyl, cyano-group, nitryl, halogen or the combination of the groups. The compound is prepared through executing fluorination in the ethane nitrile while the precursor compound of benzene sulfochloride and the metal fluoride are used as raw materials. The new kind of benzenesulphonyl fluoride which is prepared thorugh using the sulfuryl fluoride (-SO2F) group as the reacting group, the parent benzene ring as a chromosphere and the R as the auxiliary substituent group not only can be used for measuring the protein, the peptide structure and the amino acid and researching the protein or the protemics, but also can be used for developing the new medicine or used for diagnosing the difficult and complicated disease in the medical health agency. Furthermore the benzenesulphonyl fluoride of the invention can also be used as a marking agent for quality monitoring by the national medicine checking agency and the quality supervision department.

Description

Technical field: [0001] The present invention relates to a kind of benzene sulfonyl fluoride compound and its preparation method and application, specifically sulfonyl fluoride (-SO 2 F) As a reactive group, a new type of benzenesulfonyl fluoride compound (A New Kind of Benzene Sulfonyl Fluoride) with the parent benzene ring as the chromophore and R as the auxiliary substituent group and its applications in amino acids, proteins, peptides, and The application of primary amino or secondary amino, hydroxyl, phenolic hydroxyl, mercapto compounds or other chemical substances. As derivatization reagents and labeling reagents, benzenesulfonyl fluoride compounds can not only be used for the determination of protein, peptide structure and amino acid, for protein or proteomics research, but also for the research and development of new drugs, and can also be used as Diagnosis of difficult diseases, evaluation of drug efficacy, and can also be used as a labeled reagent for quality contr...

Claims

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Application Information

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IPC IPC(8): C07C309/87C07C309/86C07C303/02C07K1/13G01N33/50
Inventor 李寿椿
Owner 李寿椿
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