CN107400078A - Preparation method and application with permanent charge amber esters sugar label - Google Patents
Preparation method and application with permanent charge amber esters sugar label Download PDFInfo
- Publication number
- CN107400078A CN107400078A CN201710533481.6A CN201710533481A CN107400078A CN 107400078 A CN107400078 A CN 107400078A CN 201710533481 A CN201710533481 A CN 201710533481A CN 107400078 A CN107400078 A CN 107400078A
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- Prior art keywords
- product
- amber
- permanent charge
- label
- added
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Health & Medical Sciences (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A kind of preparation method with permanent charge amber esters sugar label of the present invention, belongs to organic synthesis and technical field of biological information.Ethylaminobenzoate passes through a series of synthesis, it is prepared into band permanent charge amber esters label, band permanent charge amber ester type compound prepared by the present invention has reaction condition gentle (45 DEG C, 40 minutes), the advantages of detection sensitivity and high derivative yield can be improved, it derives yield and reaches 98%, product usable highly effective liquid chromatogram and mass spectrum (ESI MS, MALDI ToF MS) are detected, and sensitivity is good.
Description
Technical field
The invention belongs to organic synthesis and technical field of biological information, and in particular to a kind of band permanent charge amber esters sugar
The preparation method of label.
Background technology
Played an important role in the chemically derived research learned in proteomics and sugar group, although the development of detecting instrument
Make rapid progress, but without the auxiliary of various deriving technologies, it is many it is micro existing for peptide fragments or carbohydrate be it is undetectable, not only such as
This, the sample after deriving can not show higher sensitivity and detection intensity in the detection.
The interference that can ionization and dissociation during exclude sodium ion and potassium ion of the sample with permanent charge, moreover it is possible to
Improve detection sensitivity, conventional derivative reagent TMPP (tris (2,4,6-trimethoxyphenyl) Phosphonium
Acetic acid N-hydroxysuccinimide ester) it is answering with permanent charge amber esters derivative reagent
With, sensitivity is obviously improved, and amber ester group is a more active group, and reaction condition is 40 DEG C, 20 minutes,
As mild as a dove, it is a reliable and stable derivative reagent, but the derivative reagent cost is high, limits its application, and it derives efficiency
Only about 90%.
The content of the invention
In view of the shortcomings of the prior art, the present invention provides a kind of preparation method with permanent charge amber esters sugar label
And application, in order to realize the purpose of the present invention, inventor is studied by lot of experiments and persistent exploration, is finally obtained following skill
Art scheme：
A, 1g ethylaminobenzoate is weighed in two mouthfuls of round-bottomed flasks, is added 40ml acetone solutions, is subsequently added into
3.6g Anhydrous potassium carbonates and 14.1g iodomethane, reaction are stirred at reflux 24 hours in 80 DEG C under nitrogen protection, and reaction finishes, mistake
Reaction solution is filtered, filtrate is taken, is extracted with dichloromethane, organic phase is removed water with magnesium sulfate, is concentrated by evaporation after filtering out magnesium sulfate, and product is used
Chromatograph column separating purification (mobile phase dichloromethane：Methanol=20:1) product A, is obtained.
B, 10% sodium hydroxide is added in step a gains A, 95% ethanol, 60 DEG C are flowed back 6 hours, are adjusted with 1M hydrochloric acid
PH is saved to faintly acid, reaction solution concentration, adds anhydrous propanone to dissolve, filters, take precipitation, be dried in vacuo to obtain product B；
C. according to 1 in product B:1.1 mol ratios add HOSu NHS and dicyclohexylcarbodiimide, dichloromethane
Alkane makees solvent, and mixing stands 2.5 hours, extracts, and dries, obtains product C；
D. the iodomethane of 5 times of mol ratios is added in product C, acetone as solvent, it is small to react 24 for stirring and lucifuge at room temperature
When, filtering, obtain product D.
A kind of preparation method with permanent charge amber esters sugar label, specific reaction are as follows：
A kind of application with permanent charge amber esters sugar label, the label can be applied to carbohydrate derivative.
Compared with prior art, advantages of the present invention is：
1st, band permanent charge amber ester type compound prepared by the present invention has reaction condition gently (45 DEG C, 40 minutes),
The advantages of detection sensitivity and high derivative yield can be improved, it derives yield and reaches 98%, product usable highly effective liquid phase color
Spectrum and mass spectrum (ESI-MS, MALDI-ToF-MS) are detected, and sensitivity is good, applied sample amount 50pmol (asparagine connection polysaccharide)
The good result of resolution ratio can be obtained.
2nd, the synthetic route of derivative reagent of the present invention is relatively simple, and raw material is readily available and inexpensive.
Brief description of the drawings
Fig. 1 is the sugared (malt seven of one Na ion of * bands of malt seven derived from the amber esters reagent with permanent positive charge
Sugar, the malt seven after * * derive are sugared).
Embodiment
It is the specific embodiment of the present invention below, technical scheme is done and is further described, but it is of the invention
Protection domain be not limited to these embodiments.It is every to be included in this hair without departing substantially from the change of present inventive concept or equivalent substitute
Within bright protection domain.
Embodiment 1
A, 1g ethylaminobenzoate is weighed in two mouthfuls of round-bottomed flasks, is added 40ml acetone solutions, is subsequently added into
3.6g Anhydrous potassium carbonates and 14.1g iodomethane, reaction are stirred at reflux 24 hours in 80 DEG C under nitrogen protection, and reaction finishes, mistake
Reaction solution is filtered, filtrate is taken, is extracted with dichloromethane, organic phase is removed water with magnesium sulfate, is concentrated by evaporation after filtering out magnesium sulfate, and product is used
Chromatograph column separating purification (mobile phase dichloromethane：Methanol=20:1) product A, is obtained.
B, 10% sodium hydroxide is added in step a gains A, did not had a reactant, 95% ethanol as solvent, 85 °C
Lower back flow reaction 6 hours, adjust PH with 1M hydrochloric acid and concentrated to faintly acid, reaction solution, add anhydrous propanone to dissolve, filter, take precipitation,
It is dried in vacuo to obtain product B；
C. according to 1 in product B:1.1 mol ratios add HOSu NHS and dicyclohexylcarbodiimide, dichloromethane
Alkane makees solvent, and mixing stands 2.5 hours, extracts, and dries, obtains product C；
D. the iodomethane of 5 times of mol ratios is added in product C, acetone as solvent, it is small to react 24 for stirring and lucifuge at room temperature
When, filtering, obtain product D.
Derivative experiment is carried out for the amber esters reagent with permanent positive charge of preparation, specific method is：1nmol's
The antenna standard of asparagine two sugar 30ul PBS (PH=8) dissolve, and add ambers of the 1umol with permanent positive charge of methanol dissolving
Amber ester derivative reagent, 45 DEG C of water-baths stand reaction 40 minutes, and product is purified with cellulose column, the instrument such as i.e. available mass spectrum after drying
Detection, result figure 1.
Claims (2)
1. the preparation method with permanent charge amber esters sugar label, it is characterised in that：This method comprises the following steps：
A, acetone solution is added in ethylaminobenzoate, is subsequently added into Anhydrous potassium carbonate and iodomethane, reacts and is protected in nitrogen
It is stirred at reflux 24 hours in 80 DEG C under shield, reaction finishes, and filtering reacting liquid, takes filtrate, is extracted with dichloromethane, organic phase sulphur
Sour magnesium water removal, is concentrated by evaporation after filtering out magnesium sulfate, product chromatography column separating purification, obtains product A；
B, appropriate 10% sodium hydroxide is added in product A, did not had a reactant, 95% ethanol as solvent, 60 DEG C of backflows 6 are small
When, PH is adjusted to faintly acid with hydrochloric acid, reaction solution concentration, is added anhydrous propanone to dissolve, is filtered, take precipitation, be dried in vacuo to obtain product
B；
C. according to 1 in product B:1.1 mol ratios add HOSu NHS and dicyclohexylcarbodiimide, and dichloromethane is made
Solvent, mixing stand 2.5 hours, extract, and dry, obtain product C；
D. the iodomethane of 5 times of mol ratios is added in product C, acetone as solvent, simultaneously lucifuge is reacted 24 hours for stirring at room temperature, mistake
Filter, obtains product D；
Specific reactions steps are as follows：
2. a kind of application with permanent charge amber esters sugar label, the label can be applied to carbohydrate derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710533481.6A CN107400078A (en) | 2017-07-03 | 2017-07-03 | Preparation method and application with permanent charge amber esters sugar label |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710533481.6A CN107400078A (en) | 2017-07-03 | 2017-07-03 | Preparation method and application with permanent charge amber esters sugar label |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107400078A true CN107400078A (en) | 2017-11-28 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710533481.6A Pending CN107400078A (en) | 2017-07-03 | 2017-07-03 | Preparation method and application with permanent charge amber esters sugar label |
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| Country | Link |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109232285A (en) * | 2018-10-16 | 2019-01-18 | 新乡学院 | A kind of synthetic method and application of the benzocainum disubstituted derivative with antibacterial activity |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002095393A2 (en) * | 2001-05-24 | 2002-11-28 | National Research Council Of Canada | Drug evolution: drug design at hot spots |
| WO2010135493A2 (en) * | 2009-05-20 | 2010-11-25 | Emory University | Alzheimer's disease imaging agents |
-
2017
- 2017-07-03 CN CN201710533481.6A patent/CN107400078A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002095393A2 (en) * | 2001-05-24 | 2002-11-28 | National Research Council Of Canada | Drug evolution: drug design at hot spots |
| WO2010135493A2 (en) * | 2009-05-20 | 2010-11-25 | Emory University | Alzheimer's disease imaging agents |
Non-Patent Citations (5)
| Title |
|---|
| EVELYN ZEILER ET AL.,: "Development and characterization of improved b-lactone-based anti-virulence drugs targeting ClpP", 《BIOORGANIC & MEDICINAL CHEMISTRY》 * |
| I. ALJAMMAZ ET AL.: "Rapid andone-stepradiofluorination ofbioactivepeptides:Potential PET radiopharmaceuticals", 《APPLIED RADIATIONANDISOTOPES》 * |
| XIAO-YAN TANG ET AL.,: "4-Ethoxycarbonyl-N,N,N-trimethyl-anilinium iodide", 《ACTA CRYSTALLOGRAPHICA, SECTION E: STRUCTURE REPORTS ONLINE》 * |
| XIN LIU ET AL.: "Microwave-assisted Kochetkov amination followed by permanent charge derivatization: a facile strategy for glycomics", 《CHEM. COMMUN.》 * |
| 卢庄等: "糖蛋白组学研究技术进展及其应用", 《生命的化学》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109232285A (en) * | 2018-10-16 | 2019-01-18 | 新乡学院 | A kind of synthetic method and application of the benzocainum disubstituted derivative with antibacterial activity |
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| PB01 | Publication | ||
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Application publication date: 20171128 |