4-(N, N-dimethylamino) azobenzol-4'-sulfuryl fluoride and its synthesizing method and use

A technology of dimethylamino and azobenzene, which is applied in the field of labeling reagent synthesis, can solve the problems of complex synthesis process, moisture sensitivity, and insufficient detection sensitivity, and achieve the effects of easy purification and storage, stable labeling reagents, and reliable analysis results

Inactive Publication Date: 2008-12-10
李寿椿
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Some of the labeling reagents currently used in the field of protein or proteomics research are not fully applicable to certain amino acids that make up human proteins, such as secondary amino acids, tryptophan, and cysteine
In addition, due to the low stability of derivatized products generated by the reaction of some products with amino acids, it affects the normal operation of subsequent detection operations.
Some labeling reagents are either sensitive to moisture in the air, or the detection sensitivity is not enough, or the synthesis process is complicated, or the price is expensive.

Method used

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  • 4-(N, N-dimethylamino) azobenzol-4'-sulfuryl fluoride and its synthesizing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] (1) Acetylation

[0029] Dissolve 18.6 g of aniline in a solution of 500 ml of water and 17 g of concentrated sulfuric acid, stir and heat to 50°C. Add 25 ml of acetic anhydride. When the acetic anhydride is completely dissolved, add 100 ml of a 30% sodium acetate aqueous solution and cool with ice water. The precipitated white product was filtered, washed with water, and dried at 40°C to obtain 22 g of the product acetanilide, with a yield of 81.5%. The melting point is 115°C.

[0030] (2) Chlorosulfonation

[0031] Add 58 grams of chlorosulfonic acid to a three-necked flask equipped with a stirrer, a thermometer and a hydrogen chloride gas absorber, and stir and cool to below 15°C. Add 13.5 g of acetanilide, heat to 60°C, and react for 2 hours. After cooling, pour into ice water, settle, filter, and wash until neutral. 19 grams of p-acetaminobenzenesulfonyl chloride was obtained, with a yield of 81%. The melting point is 149°C.

[0032] (3) Preparation of p-acetaminobenze...

Embodiment 2

[0041] The sodium fluoride in step (3) of Example 1 was changed to potassium fluoride, and the reaction temperature was controlled at 80-90°C. Others were the same as in Example 1. The product 4-(N,N-dimethylamino) was also obtained. ) 2 grams of azobenzene-4'-sulfonyl fluoride, with a yield of 83%.

Embodiment 3

[0043]The sodium fluoride in step (3) of Example 1 was changed to rubidium fluoride, and the reaction temperature was controlled at 80-90°C. Others were the same as in Example 1. The product 4-(N,N-dimethylamino) was also obtained. ) 2 grams of azobenzene-4'-sulfonyl fluoride, with a yield of 83%.

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Abstract

The invention discloses a novel labeling reagent 4-(N,N-dimethylamino)azobenzene-4'-sulfonyl fluoride capable of derivatization reaction with protein and amino acid and its synthesis method and the compound in protein, The application in amino acid analysis, the synthesis method of its intermediate p-acetamidobenzenesulfonyl fluoride and the application of this compound in protein and amino acid analysis. The labeling reagent uses aniline as a raw material to prepare p-acetylaminobenzenesulfonyl fluoride through acetylation, chlorosulfonation and fluorination reactions, and then hydrolyzes the p-acetylaminobenzenesulfonyl fluoride, undergoes diazotization and coupling reactions. The labeling reagent is easy to synthesize, easy to store, derivatizes with primary or secondary amino acids under mild conditions, stable derivatized products, convenient liquid phase or capillary chromatographic separation, high instrument response value, and detection sensitivity up to pmol level. Achieve the effect of chemical derivatization-instrumental detection.

Description

Technical field [0001] The invention belongs to the technical field of labeling reagent synthesis. Specifically, it relates to a new labeling reagent (New Labeling Reagent) 4-(N,N-dimethylamino)azobenzene-4'-sulfonyl fluoride and its synthesis and application. This labeling reagent can not only be used for the determination of protein primary structure, protein or proteomics research, but also for the research and development of new drugs, for the diagnosis of intractable diseases, drug efficacy evaluation and as a national drug inspection unit and quality inspection by medical and health institutions. Standard reagents for quality monitoring by the unit. Background technique [0002] Currently, some of the labeling reagents used in the field of protein or proteomics research are not fully applicable to certain amino acids that constitute human proteins, such as secondary amino acids, tryptophan, and cysteine. In addition, due to the low stability of the derivatized products form...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G01N33/52G01N33/58C07C303/32
Inventor 李寿椿
Owner 李寿椿
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