CN110372542A - One group of isotope labelling dansyl Cl and its synthetic method - Google Patents
One group of isotope labelling dansyl Cl and its synthetic method Download PDFInfo
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- CN110372542A CN110372542A CN201910586738.3A CN201910586738A CN110372542A CN 110372542 A CN110372542 A CN 110372542A CN 201910586738 A CN201910586738 A CN 201910586738A CN 110372542 A CN110372542 A CN 110372542A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/001—Acyclic or carbocyclic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/78—Halides of sulfonic acids
- C07C309/86—Halides of sulfonic acids having halosulfonyl groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/88—Halides of sulfonic acids having halosulfonyl groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
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- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
One group of isotope labelling dansyl Cl and its synthetic method, belong to the field of chemical synthesis.The present invention replaces formaldehyde and NaBH by reacting raw material 1-Naphthylamine-5-sulfonic di-methylation, using formaldehyde or isotope3CN or NaBD3The combination not of the same race of CN, isotope is introduced into the red sulfonic acid of generation, has obtained the red sulfonic acid of isotope, then to its chloride, has obtained the dansyl Cl of isotope.Isotope is had on two methyl on product amino, is introduced in synthesis process by the method that dimethyl replaces, two of them methyl is identical.Synthetic method of the present invention is simple, easy to operate, and the dansyl Cl of a variety of isotopes can be synthesized by this method, can obtain corresponding Isotopic Internal Standard object effectively to primary amine, secondary amine and phenolic hydroxyl group reaction.Can carry out multiple labelling to sample using the combination of different isotope dansyl Cls may be implemented efficient, time saving, accurate, stable qualitatively and quantitatively analysis in conjunction with LC-MS.
Description
Technical field
The invention belongs to the field of chemical synthesis, are related to the synthetic method of one group of isotope labeling reagent dansyl Cl.Pass through
This method can synthesize the dansyl Cl with different isotopes.It can be to difference using these dansyl Cls for containing isotope
Sample carries out multiple labelling, is fast and accurately qualitatively and quantitatively analyzed by liquid chromatography-mass spectrometry realization.
Background introduction
Liquid chromatography-mass spectrometry (LC-MS) can detect most of organic matters, and having become must in modern analysis
Indispensable a part, but due to the interference of complex sample mesostroma, conventional method is difficult to realize accurate quantitative analysis, and same
Accurate quantitative analysis then can be achieved in the plain internal standard method in position in conjunction with LC-MS.Isotopic Internal Standard can be efficiently against matrix effect, from altogether
The ions of eluting compounds inhibits, the difference that when sample preparation may introduce.But suitable Isotopic Internal Standard limited amount, and valence
Lattice are expensive, are not easy to obtain.Isotope is introduced into target analytes by chemically reacting using isotope labelling, is realized each
Analyte has corresponding internal standard compound.LC-MS inspection is carried out after again mixing the sample containing different isotopes or standard items
It surveys, relative quantification and absolute quantitation may be implemented.
This method passes through the formaldehyde that formaldehyde or isotope replace and sodium cyanoborohydride or cyano boron deuterate sodium, by labor
Isotope can be introduced into product pellet sulfonic acid by human relations acid di-methylation.Pass through phosphorus pentachloride (PCl again5) chlorination is carried out to it,
It is available accordingly to contain isotope dansyl Cl.Dansyl Cl is very extensive as derivatization reagent purposes, can with primary amine,
Secondary amine and phenolic hydroxyl group reaction, it is easy to operate, it is swift in response and efficiently.Sample can be carried out using different isotope dansyl Cls more
Heavy label in conjunction with LC-MS, and then realizes efficiently time saving, sensitive, accurate and reliable and stable qualitatively and quantitatively analysis.
Summary of the invention
The object of the present invention is to provide synthesis one group of isotope labeling reagent dansyl Cl method, synthesized one group
Isotope labeling reagent dansyl Cl can be used for marking amino and phenolic hydroxyl group.The present invention passes through anti-to raw material 1-Naphthylamine-5-sulfonic di-methylation
It answers, replaces formaldehyde and NaBH using formaldehyde or isotope3CN or NaBD3The combination not of the same race of CN, introduces generation for isotope
In red sulfonic acid, the red sulfonic acid of isotope has been obtained, then to its chloride, has obtained the dansyl Cl of isotope.
The technical solution adopted by the present invention are as follows:
One group of isotope labelling dansyl Cl has isotope on two methyl on amino, leads in synthesis process
The method for crossing dimethyl substitution introduces, and two of them methyl is identical.Its structure are as follows:
Wherein, R is-CDH2,-CD2H ,-13CDH2,-13CD2H, or-13CD3One of.
The synthetic method of one group of isotope labelling dansyl Cl, using 1-Naphthylamine-5-sulfonic as raw material, using formaldehyde (or isotope replace
Formaldehyde) and sodium cyanoborohydride (or cyano boron deuterate sodium) di-methylation is carried out to it, obtain isotope substitution red sulfonic acid,
It recycles phosphorus pentachloride to carry out chlorination to it, the hydroxyl in red sulfonic acid is replaced by chlorine, it is red to obtain final product isotope reagent
Sulphonyl.In the synthesis process, di-methylation is carried out to 1-Naphthylamine-5-sulfonic, the formaldehyde and cyano hydroboration replaced using formaldehyde or isotope
Sodium or cyano boron deuterate sodium, isotope are introduced into the R base of the red sulfonic acid of generation, then isotope examination can be obtained in its chlorination
Agent dansyl Cl.Specific step is as follows:
Step 1: reaction raw materials 1-Naphthylamine-5-sulfonic is dissolved in buffer, reaction raw materials concentration in buffer is 0.045-
1mmol/mL.The formaldehyde that formaldehyde or isotope replace is added, sodium cyanoborohydride NaBH is added3CN or cyano boron deuterate sodium obtain
Reaction solution reacts 2-5h at 25 DEG C, obtains the red sulfonic acid solutions of isotope substitution.With sodium cyanoborohydride NaBH3CN is
Example, the step reaction equation are as follows:
The formaldehyde or isotope replace formaldehyde to include CD2O、13CD2O、CH2O、13CH2O.The buffer solution is phosphorus
Hydrochlorate buffer solution, pH 6-8.Formaldehyde, the NaBH that 1-Naphthylamine-5-sulfonic, formaldehyde or the isotope replaces3CN or NaBD3CN tri-
The molar ratio of person is 1:4-8:2-6.
Step 2: the red sulfonic acid solutions obtained using the first step are reacted with phosphorus pentachloride in 60 DEG C after as raw material, being dried
2-4h obtains final product dansyl Cl.The molar ratio of the product pellet sulfonic acid and phosphorus pentachloride is 1:6.2-10.4.The step
Reaction equation are as follows:
The drying specifically: the red sulfonic acid solutions for obtaining the first step are transferred in round-bottomed flask, will with concentrated hydrochloric acid
PH is adjusted places 5~8h to 3~5, then by the product of acidification in freeze drier, the red sulfonic acid after being dried.
Step 3: after reaction, ice water being added and terminates reaction, then adjusts pH to 5~7 with sodium bicarbonate solution, makes to give birth to
At dansyl Cl keep stablize.Product is purified, is extracted with methylene chloride or ether.After extraction, with rotation
After evaporimeter is dry, dansyl Cl is dissolved with acetonitrile.After finally being filtered, saved under the conditions of -20 DEG C.
The invention has the benefit that the dansyl Cl of a variety of isotopes can be synthesized by this method, it can be effective
To primary amine, secondary amine and phenolic hydroxyl group reaction obtain corresponding Isotopic Internal Standard object.It can using the combination of different isotope dansyl Cls
Carrying out multiple labelling to sample may be implemented efficient, time saving, accurate, stable qualitatively and quantitatively analysis in conjunction with LC-MS.
Specific embodiment
Below in conjunction with specific embodiment, the present invention will be further described.
Embodiment 1:
1) it weighs in the 1-Naphthylamine-5-sulfonic and 10mL centrifuge tube of 0.092mmol, is dissolved with the phosphate buffer of pH=6, then plus
Enter the formalin (CH of 0.46mmol2) and 0.24mmol NaBD O3CN solution.2h is reacted at 25 DEG C, is obtained after reaction same
The red sulfonic acid solutions that position element replaces.Reaction equation is as follows:
2) above-mentioned reaction product is transferred in the round-bottomed flask of 25mL, is adjusted pH to 3, then by acidification with concentrated hydrochloric acid
Product 5h in freeze drier.The red sulfonic acid powder of dry 0.092mmol is mixed with the phosphorus pentachloride of 0.72mmol
After even, it can be obtained in 60 DEG C of solid phase reaction 4h containing there are two the dansyl Cls (D2-Dns-Cl) of D atom.Reaction equation is as follows:
3) 5mL ice water quenching reaction reagent after reaction, is added, adds sodium bicarbonate and adjusts pH=5.Dichloro is used again
After methane extracts, after Rotary Evaporators drying, dansyl Cl is dissolved with acetonitrile.After being filtered, saved in -20 DEG C.
Embodiment 2:
1) it weighs in the 1-Naphthylamine-5-sulfonic and 10mL centrifuge tube of 0.045mmol, is dissolved with the phosphate buffer of pH=8, then plus
Enter the deuterated formalin (CD of 0.18mmol2) and 0.18mmol NaBH O3CN solution.5h is reacted at 25 DEG C, obtains product
The red sulfonic acid solutions that isotope replaces.Reaction equation is as follows:
2) product among the above is transferred in the round-bottomed flask of 25mL, is adjusted pH to 5, then by acidification with concentrated hydrochloric acid
Product 6h in freeze drier.Dry 0.045mmol pellet sulfonic acid powder is uniformly mixed with the phosphorus pentachloride of 0.279mmol
Afterwards, product dansyl Cl (D4-Dns-Cl) can be obtained in 60 DEG C of solid phase reaction 2h.Reaction equation is as follows:
3) the ice water quenching reaction reagent of 5mL after reaction, is added, adds sodium bicarbonate and adjusts pH=6.Second is used again
Ether extraction.After extraction, after Rotary Evaporators drying, dansyl Cl is dissolved with acetonitrile.After being filtered, protected in -20 DEG C
It deposits.
Embodiment 3:
1) it weighs in the 1-Naphthylamine-5-sulfonic and 10mL centrifuge tube of 1mmol, is dissolved with pH=7 phosphate buffer, add 8mmol
Isotope replace formalin (13CH2) and 6mmol NaBD O3CN solution.3h is reacted at 25 DEG C, is obtained after reaction
The red sulfonic acid solutions that product isotope replaces.Reaction equation is as follows:
2) product among the above is transferred in the round-bottomed flask of 25mL, is adjusted pH to 4, then by acidification with concentrated hydrochloric acid
Product 5h in freeze drier.After mixing by the phosphorus pentachloride of dry 1mmol pellet sulfonic acid powder and 10.4mmol, in
60 DEG C of solid phase reaction 3h can be obtained product dansyl Cl (13C2D2-Dns-Cl).Reaction equation is as follows:
3) 5mL ice water quenching reaction reagent after reaction, is added, adds sodium bicarbonate and adjusts pH=6.Dichloro is used again
After methane extracts, after Rotary Evaporators drying, dansyl Cl is dissolved with acetonitrile.After being filtered, saved in -20 DEG C.
Embodiment 4:
1) it weighs in the 1-Naphthylamine-5-sulfonic and 10mL centrifuge tube of 0.47mmol, is dissolved, added with pH=7.5 phosphate buffer
Formalin that the isotope of 2.82mmol replaces (13CD2) and 1.88mmol NaBH O3CN solution.4h is reacted at 25 DEG C,
The red sulfonic acid solutions of product isotope substitution are obtained after reaction.Reaction equation is as follows:
2) above-mentioned reaction product is transferred in the round-bottomed flask of 25mL, is adjusted pH to 4, then by acidification with concentrated hydrochloric acid
Product 8h in freeze drier.After mixing by the phosphorus pentachloride of dry 0.47mmol pellet sulfonic acid powder and 4.7mmol,
In 60 DEG C of solid phase reaction 4h can be obtained product dansyl Cl (13C2D4-Dns-Cl).Reaction equation is as follows:
3) 5mL ice water quenching reaction reagent after reaction, is added, adds sodium bicarbonate and adjusts pH=7.Dichloro is used again
After methane extracts, after Rotary Evaporators drying, dansyl Cl is dissolved with acetonitrile.After being filtered, saved in -20 DEG C.
Embodiment 5:
1) it weighs in the 1-Naphthylamine-5-sulfonic and 10mL centrifuge tube of 0.184mmol, is dissolved with pH=6.5 phosphate buffer, then plus
Enter 0.736mmol isotope replace formalin (13CD2) and 0.368mmol NaBD O3CN solution.It is anti-at 25 DEG C
4h is answered, the red sulfonic acid solutions of product isotope substitution are obtained.Reaction equation is as follows:
2) product in is transferred in the round-bottomed flask of 25mL, with concentrated hydrochloric acid by pH adjust to 3, then by the product of acidification in
7h in freeze drier.After mixing by the phosphorus pentachloride of dry 0.184mmol pellet sulfonic acid powder and 1.84mmol, in 60
DEG C solid phase reaction 4h can be obtained product dansyl Cl (13C2D6-Dns-Cl).Reaction equation is as follows:
3) 5mL ice water quenching reaction reagent after reaction, is added, the sodium bicarbonate for adding 8.3mmol adjusts pH=
6.After being extracted again with ether, after Rotary Evaporators drying, dansyl Cl is dissolved with acetonitrile.After being filtered, in -20 DEG C
It saves.
Embodiment described above only expresses embodiments of the present invention, and but it cannot be understood as to the invention patent
Range limitation.It should be pointed out that for those skilled in the art, without departing from the inventive concept of the premise, also
Several modifications and improvements can be made, these are all belonged to the scope of protection of the present invention.
Claims (6)
1. the synthetic method of one group of isotope labelling dansyl Cl, which comprises the following steps:
Step 1: reaction raw materials 1-Naphthylamine-5-sulfonic is dissolved in buffer, reaction raw materials concentration in buffer is 0.045-1mmol/
mL；The formaldehyde that formaldehyde or isotope replace is added, adds sodium cyanoborohydride NaBH3CN or cyano boron deuterate sodium are reacted
Solution reacts 2-5h at 25 DEG C, obtains the red sulfonic acid solutions of isotope substitution；With sodium cyanoborohydride NaBH3It, should for CN
Walk reaction equation are as follows:
Formaldehyde, the NaBH that 1-Naphthylamine-5-sulfonic, formaldehyde or the isotope replaces3CN or NaBD3The molar ratio of CN three is 1:4-8:2-
6；
Step 2: the red sulfonic acid solutions obtained using the first step, which as raw material, are dried, reacts 2-4h in 60 DEG C with phosphorus pentachloride afterwards,
Obtain final product dansyl Cl；The molar ratio of the product pellet sulfonic acid and phosphorus pentachloride is 1:6.2-10.4；Step reaction
Formula are as follows:
Step 3: after reaction, ice water is added and terminates reaction, then adjusts pH to 5~7 with sodium bicarbonate solution, to product into
After row purifying, extraction are dry, product is obtained.
2. the synthetic method of one group of isotope labelling dansyl Cl according to claim 1, which is characterized in that first step institute
The formaldehyde or isotope stated replace formaldehyde to include CD2O、13CD2O、CH2O、13CH2O。
3. the synthetic method of one group of isotope labelling dansyl Cl according to claim 1 or 2, which is characterized in that first
The step buffer solution is phosphate buffer solution, pH 6-8.
4. the synthetic method of one group of isotope labelling dansyl Cl according to claim 1 or 2, which is characterized in that second
The step drying specifically: the red sulfonic acid solutions for obtaining the first step are transferred in round-bottomed flask, are adjusted pH with concentrated hydrochloric acid
5~8h is placed in freeze drier to 3~5, then by the product of acidification, the red sulfonic acid after being dried；.
5. the synthetic method of one group of isotope labelling dansyl Cl according to claim 3, which is characterized in that second step institute
The drying stated specifically: the red sulfonic acid solutions for obtaining the first step are transferred in round-bottomed flask, adjusted pH to 3 with concentrated hydrochloric acid~
5, then the product of acidification is placed into 5~8h in freeze drier, the red sulfonic acid after being dried.
6. the isotope labelling dansyl Cl obtained using any synthetic method of claim 1-5, which is characterized in that institute
The position element stated marks dansyl Cl, and isotope is had on two methyl on amino, is taken in synthesis process by dimethyl
The method in generation introduces, and two of them methyl is identical；Its structure are as follows:
Wherein, R is-CDH2,-CD2H ,-13CDH2,-13CD2H, or-13CD3One of.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111349028A (en) * | 2020-03-11 | 2020-06-30 | 苏州根岸生物科技有限责任公司 | Synthesis method of dansyl chloride for preparing fluorescent probe |
| CN113620847A (en) * | 2021-08-11 | 2021-11-09 | 复旦大学 | Naphthalenesulfonyl compounds, preparation method and application thereof |
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| CN102887841A (en) * | 2012-11-02 | 2013-01-23 | 天津希恩思生化科技有限公司 | Preparation method of compound dansyl chloride |
| CN104945285A (en) * | 2015-05-26 | 2015-09-30 | 无锡贝塔医药科技有限公司 | Synthesis method of isotope labeled dansyl chloride-13C2 |
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2019
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| CN102887841A (en) * | 2012-11-02 | 2013-01-23 | 天津希恩思生化科技有限公司 | Preparation method of compound dansyl chloride |
| CN104945285A (en) * | 2015-05-26 | 2015-09-30 | 无锡贝塔医药科技有限公司 | Synthesis method of isotope labeled dansyl chloride-13C2 |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111349028A (en) * | 2020-03-11 | 2020-06-30 | 苏州根岸生物科技有限责任公司 | Synthesis method of dansyl chloride for preparing fluorescent probe |
| CN111349028B (en) * | 2020-03-11 | 2022-02-11 | 苏州根岸生物科技有限责任公司 | Synthesis method of dansyl chloride for preparing fluorescent probe |
| CN113620847A (en) * | 2021-08-11 | 2021-11-09 | 复旦大学 | Naphthalenesulfonyl compounds, preparation method and application thereof |
| CN113620847B (en) * | 2021-08-11 | 2022-08-09 | 复旦大学 | Naphthalenesulfonyl compounds, preparation method and application thereof |
| WO2023016517A1 (en) * | 2021-08-11 | 2023-02-16 | 复旦大学 | Naphthalenesulfonyl compound, preparation method therefor, and application thereof |
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Application publication date: 20191025 |