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1, 3-deuterated dansyl chloride and preparation method and application thereof

A technology of dansyl chloride and deuterium, applied in the field of isotope derivatization reagents, can solve problems such as differences in retention time and large difference in mass number of dansyl chloride

Active Publication Date: 2020-12-01
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are 6-deuterated dansyl chloride derivatization reagents, but due to the large mass difference with unlabeled dansyl chloride, there is still a certain retention time difference. The ideal isotope derivatization reagent should have a difference of 3 Daltons, and there is no report of 3 deuterated dansyl chloride derivatization reagents in the prior art

Method used

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  • 1, 3-deuterated dansyl chloride and preparation method and application thereof
  • 1, 3-deuterated dansyl chloride and preparation method and application thereof
  • 1, 3-deuterated dansyl chloride and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Prepare the reaction raw materials according to the following dosage ratio:

[0062] The mol ratio of paraformaldehyde and 5-amino-1-naphthalenesulfonic acid is 4.9:1;

[0063] The mol ratio of sodium borohydride and 5-amino-1-naphthalenesulfonic acid is 2.0:1;

[0064] The mol ratio of deuteroiodomethane and reducing material B is 5.2:1;

[0065] The mol ratio of phosphorus oxychloride, phosphorus pentachloride and deuterium solid material is 9.1:2.2:1, and wherein, the amount of each component material is calculated with the mark molecular weight of commercially available product as the criterion, and the relative molecular weight of each component or The density parameters are listed in the brackets of the following steps, and the specific preparation process is:

[0066] Step 1: Weigh 1.5g (223.25 / 0.0067mol) of 5-amino-1-naphthalenesulfonic acid into 30mL of methanol, and then add 2.17g (54.0 / 0.0434mol) of sodium methoxide. When the solution is brownish red, add ...

Embodiment 2

[0080] Prepare 3-deuterated dansyl chloride in the manner of Example 1, except that:

[0081] The mol ratio of paraformaldehyde and 5-amino-1-naphthalenesulfonic acid is 4:1;

[0082] The mol ratio of sodium borohydride and 5-amino-1-naphthalenesulfonic acid is 2:1;

[0083] The mol ratio of deuteroiodomethane and reducing material B is 4:1;

[0084]The mol ratio of phosphorus oxychloride, phosphorus pentachloride and deuterated solid material is 7:3:1;

[0085] The temperature of the first substitution reaction is 37° C., and the reaction time is 1.5 h; the yield of the obtained target product is 75%, and the purity is 80%.

Embodiment 3

[0087] Prepare 3-deuterated dansyl chloride in the manner of Example 1, except that:

[0088] The mol ratio of paraformaldehyde and 5-amino-1-naphthalenesulfonic acid is 3.5:1;

[0089] The mol ratio of sodium borohydride and 5-amino-1-naphthalenesulfonic acid is 2.7:1;

[0090] The mol ratio of deuterated methyl iodide and reducing material B is 4.2:1;

[0091] The mol ratio of phosphorus oxychloride, phosphorus pentachloride and deuterated solid material is 8:1.5:1;

[0092] The temperature of the first substitution reaction was 30° C., and the time was 2.5 h; the yield of the obtained target product was 78%, and the purity was 63%.

[0093] As can be seen from the above examples, the method provided by the present invention can prepare 3-deuterated dansyl chloride, the reaction raw materials are easy to obtain, the preparation method is simple and easy to control, and the yield is high, reaching more than 75%; the overall reliability of the preparation method is high, and...

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Abstract

The invention belongs to the technical field of isotope derivatization reagents, and particularly relates to 3-deuterated dansyl chloride and a preparation method and application thereof. According tothe preparation method, 3-deuterated dansyl chloride can be prepared from reaction raw materials including 5-amino-1-naphthalene sulfonic acid, paraformaldehyde, sodium borohydride, sodium hydride, deuterated methyl iodide, phosphorus oxychloride and phosphorus pentachloride. According to the preparation method, the raw materials are easy to obtain, few intermediate products are produced, and the3-deuterated dansyl chloride derivative reagent can be obtained and can be used for fluorescence detection or metabonomics analysis and research.

Description

technical field [0001] The invention belongs to the technical field of isotope derivatization reagents, in particular to 3-deuterated dansyl chloride and its preparation method and application. Background technique [0002] In metabolomics research, small molecular compounds contained in biological samples can reflect the metabolic state of the body, and dansyl chloride can specifically bind to the active hydrogen atoms of small molecular compounds to enhance the mass spectrometric response of small molecular compounds. The combination of isotope dansyl chloride derivatization reagent and dansyl chloride derivatization reagent has outstanding advantages in qualitative identification of metabolites and screening of unknown metabolites; and deuterated dansyl chloride derivatization reagent combined with standard substances can be more It is convenient to obtain the isotope standard of the derivatized standard substance, which is used to supplement the co-elution and matrix eff...

Claims

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Application Information

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IPC IPC(8): C07C303/02C07C309/88C07C303/22C07C309/47G01N21/64C07B59/00
CPCC07C303/02C07C303/22G01N21/6428C07B59/001C07B2200/05C07C309/88C07C309/47
Inventor 再帕尔阿不力孜张瑞萍汪满江措王玉成张国宁臧清策贺玖明刘家兴
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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