CN108929241A - For the probe compound of fluorescence identifying amino acid enantiomer and its synthesis and application - Google Patents
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Abstract
The present invention provides a kind of probe compounds for being used for fluorescence identifying amino acid enantiomer, it is that square dimethyl phthalate is dissolved in anhydrous methanol, the methanol solution of phenylalanine ethyl ester, phenylalanine benzyl ester, phenylalanine ter-butyl ester is added dropwise respectively, it is stirred at room temperature 20 after dripping off ~ for 24 hours, filtering, filter residue is repeatedly washed with ethyl acetate, obtains probe compound a, b, c respectively.In the ethanol-water solution of chiral probe compound a, c, respectively and D-PROLINE, D-PROLINE, which is added, can be such that the fluorescence intensity of solution weakens, L-PROLINE, which is added, can be such that the fluorescence of solution is remarkably reinforced, therefore probe compound a, c have preferable recognition effect to two kinds of enantiomters of proline.In the ethanol-water solution of probe compound b, Valine, which is added, can be such that the fluorescence of solution obviously weakens；And the fluorescence that D-Val solution is added is constant.Therefore, needle compound b has preferable recognition effect to two kinds of enantiomters of valine.
Description
Technical field
The present invention provides a kind of probe compound more particularly to a kind of probes for fluorescence identifying amino acid enantiomer
Compound, the present invention also relate to the synthetic method and concrete application of the probe compound, belong to chemosynthesis technical field
With chiral Recognition detection technique field.
Background technique
Enantiomter makes it in achirality environment due to the high similarity (only space conformation is different) in its structure
Under physicochemical property it is nearly identical, therefore the identification of chipal compounds, detection and separation are very challenging.Currently,
The detection separation method of comparative maturity mainly includes high performance liquid chromatography, Capillary Electrophoresis and chromatography of gases.However these methods
Also have disadvantages that, it is with high costs such as instrument complexity, test period is longer lead to not meet it is high-throughput in medicament research and development
In addition the demand of screening can not realize real-time, in situ detection.Optical analysis side based on fluorescence spectrum and uv-vis spectra
Method can overcome disadvantage mentioned above very well, therefore be developed in a series of chiral fluorescent probe molecules of past two ten years
Come, identification and detection for chipal compounds.Its testing principle be the chiral probe molecule property of can choose in enantiomer
A kind of combination, by fluorescent quenching, fluorescence enhancement, optical activity variation and uv-vis spectra variation generate optical signalling,
To achieve the purpose that detection.Structure is complicated mostly for chiral fluorescent probe molecule reported in the literature at present, and synthetic route is longer, valence
Lattice are high.
Summary of the invention
The object of the present invention is to provide the probe compounds of a kind of fluorescence identifying amino acid enantiomer；
It is a further object of the present invention to provide a kind of synthetic methods of above-mentioned probe compound；
Another object of the present invention is to provide above-mentioned probe compound in the concrete application of fluorescence identifying amino acid enantiomer.
One, probe compound
Probe compound of the present invention, structural formula are as follows:
R=Et, probe compound are denoted as a, R=Bn, and probe compound is denoted as b, and R=tBu, probe compound are denoted as c.
The synthesis of probe compound: being that square dimethyl phthalate is dissolved in anhydrous methanol, and the methanol of amino-acid ester is added dropwise respectively
Solution, is stirred at room temperature 20 ~ for 24 hours after dripping off, filtering, filter residue is repeatedly washed with ethyl acetate, respectively probe compound.
Amino-acid ester is phenylalanine ethyl ester, phenylalanine benzyl ester, phenylalanine ter-butyl ester.Square dimethyl phthalate and amino acid
The molar ratio of ester is 1:2 ~ 1:3.
Probe molecule reaction equation is as follows:
The structure exterior syndrome of probe compound a, b, c are shown in Fig. 1 ~ 6.
Two, identification of probe compound a, b, the c for amino acid enantiomer
Using ethyl alcohol: water=9:1(volume ratio) mixture as solvent, respectively by probe compound a, b, c and detected amino acid
Enantiomerism (L-phenylalanine, D-phenylalanine；Valine, D-Val；L-PROLINE, D-PROLINE.) be configured to it is dense
Degree is 2.0 × 10-5 The solution of mol/L.Then by probe compound respectively with two kinds of enantiomters of natural amino acid with 1:
1 molar ratio mixing, stands 1h.With Fluorescence Spectrometer detection probe compound, probe compound+L- isomers, probe chemical combination
The fluorescence intensity of object+D- isomers, detects its recognition effect.
The fluorescence response figure of probe compound identification amino acid enantiomerism is shown in Fig. 7 ~ Figure 15.It can be sent out by testing us
Existing: (1) after mixing L-PROLINE with probe compound a, fluorescence intensity obviously weakens, and by D-PROLINE and probe compound
After a mixing, fluorescence intensity is remarkably reinforced.Therefore, probe compound a has preferable knowledge to two kinds of enantiomters of proline
Other effect.(2) after mixing Valine with probe compound b, fluorescence intensity obviously weakens, and by D-Val and probe
After closing object b mixing, fluorescence intensity does not have significant change.Therefore, probe compound b can be used for two kinds of fluorescence identifying valine it is right
Reflect isomers.(3) after mixing L-PROLINE with probe compound c, fluorescence intensity slightly weakens, and by D-PROLINE and probe
After compound c mixing, fluorescence intensity is remarkably reinforced, therefore, probe compound c to two kinds of enantiomters of proline have compared with
Good recognition effect.
Detailed description of the invention
Fig. 1 is the nucleus magnetic hydrogen spectrum of probe compound a.
The nuclear-magnetism carbon that Fig. 2 is probe compound a is composed.
Fig. 3 is the nucleus magnetic hydrogen spectrum of probe compound b.
The nuclear-magnetism carbon that Fig. 4 is probe compound b is composed.
Fig. 5 is the nucleus magnetic hydrogen spectrum of probe compound c.
The nuclear-magnetism carbon that Fig. 6 is probe compound c is composed.
Fig. 7 is the fluorescence response figure that probe compound a identifies phenylalanine.
Fig. 8 is the fluorescence response figure that probe compound a identifies valine.
Fig. 9 is the fluorescence response figure that probe compound a identifies proline.
Figure 10 is the fluorescence response figure that probe compound b identifies phenylalanine.
Figure 11 is the fluorescence response figure that probe compound b identifies valine.
Figure 12 is the fluorescence response figure that probe compound b identifies proline.
Figure 13 is the fluorescence response figure that probe compound c identifies phenylalanine.
Figure 14 is the fluorescence response figure that probe compound c identifies valine.
Figure 15 is the fluorescence response figure that probe compound c identifies proline.
Specific embodiment
Below by specific embodiment to the synthesis of probe compound a, b, c of the present invention and to natural amino acid mapping
The fluorescence identifying performance of body is described further.
Embodiment one
1, the synthesis of probe compound a
(1) L-phenylalanine (20.0mmol) and dehydrated alcohol the synthesis of L-phenylalanine ethyl ester: are added into reaction kettle
125mL, ice bath is cooling, thionyl chloride (20mL) is slowly added dropwise under stirring, 20min is dripped off, and is stirred for 2h, then heats to 80 DEG C
React 5h.50ml ether is added after cooling, solution muddiness occurs, mixture is then had crystalline solid precipitation in 0 DEG C of 2 h of refrigeration.
Filter and collect solid, recrystallized with dehydrated alcohol-ether mixtures, 30mL water is added in obtained product, with triethylamine tune pH=
9, it is extracted with ethyl acetate (30mL × 3), merges organic phase, successively use saturated salt solution and water washing, it is dry with anhydrous magnesium sulfate
Dry, decompression steams ethyl acetate, obtains yellow oil --- L-phenylalanine ethyl ester 2.5g, yield 65%.Synthesis formula is as follows:
(2) synthesis of probe molecule a: square dimethyl phthalate (3.0mmol) is added in 50mL reaction kettle, and 20mL is added without water beetle
Methanol (10mL) solution of L-phenylalanine ethyl ester (6.0mmol) is added dropwise in alcohol, is stirred at room temperature for 24 hours, filtering, filter residue acetic acid second
Ester repeatedly washs, products obtained therefrom 0.77g；When freezing 2 h after mother liquor concentrations half, filtration washing, obtains product 0.08g again,
Yield 80%.Synthesis formula is as follows:
The nucleus magnetic hydrogen spectrum of probe compound a, nuclear-magnetism carbon spectrum are shown in Fig. 1, Fig. 2.
2, probe compound a identifies proline enantiomers
Using ethyl alcohol: water=9:1(volume ratio) mixture as solvent, respectively by probe compound a and detected material native amino
It is 2.0 × 10 that sour (L-PROLINE, D-PROLINE), which is configured to concentration,-5 The solution of mol/L.Then by probe compound a respectively with
Two kinds of enantiomter 1:1 of natural amino acid are mixed, and stand 1h.With Fluorescence Spectrometer detection probe compound a, probe chemical combination
Object+L-PROLINE, probe compound+D-PROLINE fluorescence intensity, detect its recognition effect.
Experimental result: after L-PROLINE is mixed with probe compound a, fluorescence intensity obviously weakens, and by D-PROLINE
After mixing with probe compound a, fluorescence intensity is remarkably reinforced, the fluorescence intensity ratio I of the twoD:ILReach 1.2(and see Fig. 9).
It is above-mentioned the experiment results show that being separately added into L-PROLINE and D- dried meat in the ethanol-water solution of probe compound a
Propylhomoserin, if the fluorescence of solution is remarkably reinforced, illustrate to be added is D-PROLINE；If the fluorescence intensity of solution weakens, illustrate to be added
Be L-PROLINE.
Embodiment two
1, the synthesis of probe compound b
(1) L-phenylalanine (20.0mmol) and anhydrous benzyl alcohol 125mL the synthesis of phenylalanine benzyl ester: are added into reaction kettle
(1.2mol), ice bath is cooling, thionyl chloride (20mL, 420mmol) is slowly added dropwise under stirring, 20min is dripped off, and is stirred for 2h, so
After be warming up to 80 DEG C of reaction 5h.Be added 50ml ether after cooling, solution occur it is muddy, then by mixture in 0 DEG C of 2 h of refrigeration,
There is crystalline solid precipitation.Solid is filtered and collected, is recrystallized with dehydrated alcohol-ether mixtures, 30mL water is added in obtained product,
It with triethylamine tune pH=9, is extracted with ethyl acetate (30mL × 3), merges organic phase, successively use saturated salt solution and water washing, used
Anhydrous magnesium sulfate is dry, and decompression steams ethyl acetate, obtains yellow oil --- L-phenylalanine benzyl ester, yield 56%.Phenylpropyl alcohol
The synthetic reaction formula of propylhomoserin benzyl ester is as follows:
(2) synthesis of probe molecule b: square dimethyl phthalate (3.0mmol) is added in 50mL reaction kettle, and 20mL is added without water beetle
Methanol (10mL) solution of phenylalanine benzyl ester (6.0mmol) is added dropwise in alcohol, is stirred at room temperature for 24 hours, filtering, filter residue ethyl acetate
Repeatedly washing, obtains product probe molecule b 0.7g；When freezing 2 h after mother liquor concentrations half, filtration washing, is produced again again
Product probe molecule b 0.45g adds up to yield 65%.
The synthesis formula of probe molecule b is as follows:
The nucleus magnetic hydrogen spectrum of probe compound b, nuclear-magnetism carbon spectrum are shown in Fig. 3, Fig. 4.
2, probe compound b identification identification valine
Using ethyl alcohol: water=9:1(volume ratio) mixture as solvent, respectively by probe compound b and detected material native amino
It is 2.0 × 10 that sour (Valine, D-Val), which is configured to concentration,-5 The solution of mol/L.Then by probe compound b respectively with
Two kinds of enantiomter 1:1 of natural amino acid are mixed, and stand 1h.With Fluorescence Spectrometer detection probe compound b, probe chemical combination
Object+Valine, probe compound+D-Val fluorescence intensity, detect its recognition effect.
Experimental result: after Valine is mixed with probe compound b, fluorescence intensity obviously weakens, and by D-Val
After mixing with probe compound b, fluorescence intensity does not have significant change.
It is above-mentioned the experiment results show that being separately added into Valine and D- figured silk fabrics in the ethanol-water solution of probe compound b
Propylhomoserin, if the fluorescence of solution obviously weakens, illustrate to be added is Valine；If the fluorescence of solution is constant, illustrate be added be
D-Val (referring to Figure 11).
Embodiment three
1, the synthesis of probe molecule c
(1) synthesis of phenylalanine ter-butyl ester: by L-phenylalanine (20.0mmol) molten tert-butyl acetate in 100mL
(750mmol), ice bath is cooling, and perchloric acid (1.8mL, 30mmol) is slowly added dropwise under stirring, is warmed to room temperature naturally after dripping off, and stirs
12 h.Then reaction solution is adjusted to 9 with 10% wet chemical tune pH value, dichloro successively with water, 1.0mol/L salt acid elution
Methane extracts three times, merges organic phase, and anhydrous sodium sulfate is dry, and concentration, gained crude product uses column chromatography to obtain yellow oily
Object phenylalanine ter-butyl ester, yield 69%.The synthetic reaction formula of phenylalanine ter-butyl ester is as follows:
(2) synthesis of probe molecule c: square dimethyl phthalate (3.0mmol) is dissolved in 20mL anhydrous methanol, phenylalanine ethyl ester is added dropwise
Methanol (10mL) solution of (6.0mmol) is stirred at room temperature for 24 hours, and filtering, filter residue is repeatedly washed with ethyl acetate, obtains product probe
Molecule c 0.6g freezes 2 h after mother liquor concentrations half, filters again, washs, again portioned product probe molecule c 0.34g, closes
Count yield 60%.
The synthesis formula of probe molecule c is as follows:
The nucleus magnetic hydrogen spectrum of probe compound c, nuclear-magnetism carbon spectrum are shown in Fig. 5, Fig. 6.
2, probe compound c identifies proline
Using ethyl alcohol: water=9:1(volume ratio) mixture as solvent, by probe compound c, L-PROLINE, D-PROLINE configure
It is 2.0 × 10 at concentration-5Mol/L solution.Then by probe compound c respectively with two kinds of enantiomters 1 of natural amino acid:
1 mixing, stands 1h.With Fluorescence Spectrometer detection probe compound c, probe compound c+L- proline, probe compound c+ D-
The fluorescence intensity of proline detects its recognition effect.
Test result is shown, after L-PROLINE is added, the fluorescence intensity of probe c solution weakens, after D-phenylalanine is added,
The fluorescence intensity of 1c enhances, the fluorescence intensity ratio I of the twoD:ILReach 1.3.
It is above-mentioned the experiment results show that being separately added into L-PROLINE and D- dried meat in the ethanol-water solution of probe compound c
Propylhomoserin, if the fluorescence of solution is remarkably reinforced, illustrate to be added is D-PROLINE；If the fluorescence intensity of solution weakens, illustrate to be added
Be L-PROLINE (referring to Figure 15).
In the various embodiments described above, the examination such as square dimethyl phthalate, alanine ethyl ester, phenylalanine benzyl ester, phenylalanine ter-butyl ester
Agent can also be prepared by buying in the market by the above method.
Claims (8)
1. being used for the probe compound of fluorescence identifying amino acid enantiomer, structural formula is as follows:
R=Et, probe compound are denoted as a, R=Bn, and probe compound is denoted as b, and R=tBu, probe compound are denoted as c.
2. the synthetic method for the probe compound of fluorescence identifying amino acid enantiomer as described in claim 1, is by square acid
Dimethyl ester is dissolved in anhydrous methanol, and the methanol solution of amino-acid ester is added dropwise, it is stirred at room temperature 20 after dripping off ~ for 24 hours, filtering, filter residue is used
Ethyl acetate repeatedly washs, and obtains probe compound.
3. the synthetic method for the probe compound of fluorescence identifying amino acid enantiomer, feature exist as described in claim 1
In: the amino-acid ester phenylalanine ethyl ester, phenylalanine benzyl ester, phenylalanine ter-butyl ester.
4. the synthetic method for the probe compound of fluorescence identifying amino acid enantiomer, feature exist as described in claim 1
In: the molar ratio of square dimethyl phthalate and amino-acid ester is 1:2 ~ 1:3.
5. probe compound as described in claim 1 is used for fluorescence identifying amino acid enantiomer.
6. probe compound as claimed in claim 5 is used for fluorescence identifying amino acid enantiomer, it is characterised in that: in chiral probe
Compound a, c ethanol-water solution in, be separately added into L-PROLINE and D-PROLINE, if the fluorescence of solution is remarkably reinforced, explanation
What is be added is D-PROLINE；If the fluorescence intensity of solution weakens, illustrate to be added is L-PROLINE.
7. probe compound as claimed in claim 5 is used for fluorescence identifying amino acid enantiomer, it is characterised in that: in probe chemical combination
In the ethanol-water solution of object b, it is separately added into Valine and D-Val, if the fluorescence of solution obviously weakens, illustrates addition
It is Valine；If the fluorescence intensity of solution is almost unchanged, illustrate to be added is D-Val.
8. probe compound is used for fluorescence identifying amino acid enantiomer as described in claim 6,7, it is characterised in that: alcohol-water
In solution, ethyl alcohol and water volume ratio are 8:1 ~ 9:1.
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| JPH05229999A (en) * | 1992-02-20 | 1993-09-07 | Kyowa Hakko Kogyo Co Ltd | Cyclobutenedione derivative |
| WO2003014371A1 (en) * | 2001-08-10 | 2003-02-20 | Isis Innovation Limited | Method for preparing ester linked peptide-carbohydrate conjugates |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH05229999A (en) * | 1992-02-20 | 1993-09-07 | Kyowa Hakko Kogyo Co Ltd | Cyclobutenedione derivative |
| WO2003014371A1 (en) * | 2001-08-10 | 2003-02-20 | Isis Innovation Limited | Method for preparing ester linked peptide-carbohydrate conjugates |
| US20040208883A1 (en) * | 2001-08-10 | 2004-10-21 | Davis Benjamin Guy | Method for preparing ester linked peptide-carbohydrate conjugates |
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