CN107098821A - The quaternized aromatic hydrocarbons of post 5 and synthesis and the application of fluoroscopic examination L tryptophans - Google Patents
The quaternized aromatic hydrocarbons of post 5 and synthesis and the application of fluoroscopic examination L tryptophans Download PDFInfo
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Abstract
The invention discloses a kind of quaternized aromatic hydrocarbons of post 5, be by the aromatic hydrocarbons of symmetry copolymerization post 5 and trimethylamine in ethanol back flow reaction and obtain.The quaternized aromatic hydrocarbons of post 5 has good water solubility, and provides a good cavity structure matched with L Trp, so as to complete host-guest inclusion so that its fluorescent quenching.Therefore, L Trp identification can be used for as new identification system.Fluorescence property research shows, in the aqueous dimethyl sulphoxide solution of the quaternized aromatic hydrocarbons of post 5, it is separately added into 20 kinds of native amino acid solutions for maintaining that key effect is played in physiology course, only L Trp addition can make the fluorescent quenching of the quaternized arene solution of post 5, and the addition of remaining cation does not influence on the fluorescence of the quaternized arene solution of post 5.Moreover, the fluorescence intensity of the aqueous dimethyl sulphoxide solution of the quaternized aromatic hydrocarbons of post 5 and L Trp concentration are in good linear relationship.
Description
Technical field
The present invention relates to a kind of synthetic method of the quaternized aromatic hydrocarbons of post 5, the present invention also relates to the quaternized aromatic hydrocarbons of post 5
In the application of fluorescence identifying L-Trp, belong to the synthesis technical field of compound and the detection technique field of amino acid.
Background technology
20 kinds of natural amino acids, as the construction unit and important metabolin of protein, in physiology course is maintained
Play key effect, such as specific immunity, regulation metabolism, nerve modulation, organ dysfunction etc..Each amino acid deletions can draw
Play corresponding disease.Because amino acid plays an important role in chemistry and biology, their identification and detection has caused
The extensive concern of scientist.In amino acid, L-Trp（L-Trp）It is amino acid important in vivo, it can be effectively pre-
Anti- eyelid and depression, improve sleep and mood regulation.Therefore, it is necessary to research and develop energetically for detecting L-Trp's
Sensor.
Determining the method for amino acid has it has been reported that such as high performance liquid chromatography, AAS, electrochemistry, mass spectrography and electricity
Swimming method.However, the complicated pretreatment of the high cost of these methods, muting sensitivity and sample.Fluoroscopic examination is constantly subjected to many
The concern of person, because its cost is low, sensitivity is high.Therefore, synthesis detection L-Trp fluorescent optical sensor is used with particularly significant
Meaning.
Post aromatic hydrocarbons has been shown very outstanding as the new supermolecule main block compound of a class in terms of host-guest chemistry
Effect.By the modification to post aromatic hydrocarbons structure, many host-guest chemistry systems are developed well.It is well known that the virtue of post 5
Hydrocarbon provides a big pi-electron cavity well, so with certain assembling ability.L-Trp is due to itself unique indyl
Group, can occur Subjective and Objective complexing with the pi-electron cavity of the aromatic hydrocarbons of post 5.Therefore, can be as new using the unique texture of post aromatic hydrocarbons
Identification system be used for L-Trp identification.CN201610200496.6（The achievement in research of our seminar's early stages）Disclose pair
The title property aromatic hydrocarbons of post 5 is used as the application of acceptor colorimetric fluorescence identifying L-Trp, the i.e. DMSO/ in the aromatic hydrocarbons of symmetry post 5
CH3CH2OH/H2In O systems, L-type amino acid Gly, Asp, Met, Pro, Thr, Leu, Val, Glu, Cys, Tys, Ala are added,
The addition of Gln, Asn, Ser, Phe, Ile, Lys, Arg, His solution, only L-Trp, can make the aromatic hydrocarbons of symmetry post 5
Solution fluorescence is opened.Although the aromatic hydrocarbons of symmetry post 5 unicity can detect L-Trp in L-type essential amino acid in 20,
Because its identification is in DMSO/CH3CH2OH/H2Carried out in O systems, solution system is relative complex, and water content is relatively fewer；
Meanwhile, main body is insoluble in water, and slow for the response speed of L-Trp（Response time is 20 minutes or so）.These
Factor greatly affected the operation of identification.
The content of the invention
It is an object of the invention to provide a kind of synthetic method of the quaternized aromatic hydrocarbons of post 5；
It is a further object of the present invention to provide the quaternized aromatic hydrocarbons of post 5 fluoroscopic examination L-Trp application.
First, the synthesis of the quaternized aromatic hydrocarbons of post 5
Using ethanol as solvent, the aromatic hydrocarbons of symmetry copolymerization post 5 is with trimethylamine with 1:5~1:8 mol ratio in 78 DEG C of back flow reactions 20 ~
24h, is cooled to room temperature, and the dry solvent of vacuum rotary steam obtains white solid, washed with ethanol, obtains the quaternized aromatic hydrocarbons of post 5, mark
For：BTAP5.Its structural formula is：
。
2nd, the amino acid recognition performance of the quaternized aromatic hydrocarbons of post 5
1st, to the fluorescence identifying performance of amino acid
0.5mL BTAP5 dimethyl sulphoxide solution is pipetted respectively（2×10-3mol·L-1）In a series of 10mL colorimetric cylinders,
Then L-Trp, β-Ala, L-Arg, L-Cys, L-Gly, L-Lys, L-Pro, L-Met, L- are added in BTAP5 solution respectively
Thr, L-Ser, L-His, L-Val, L-Tyr, L-Asn, L-Glu, L-Gln, L-Ile, L-Phe, DL-Asp and L-Leu's is water-soluble
Liquid（0.002mol·L-1）2.5mL, plus distilled water 1.0mL, then it is diluted to dimethyl sulfoxide (DMSO) 5mL, now BTAP5 concentration
For 2 × 10-4mol·L-1, amino acid concentration is 5 times of BTAP5 concentration.Placed after well mixed, observation acceptor is to amino acid
Response.
It was found that, in BTAP5 solution, it is separately added into after above-mentioned Freamine Ⅲ, in corresponding ultraviolet spectra,
There is absworption peak at 255nm.In its corresponding fluorescence emission spectrum, only L-Trp addition makes hairs of the BTAP5 at 330nm
Penetrate peak disappearance（Fig. 1）, and the addition of remaining cation has no significant effect to the fluorescence spectrum of BTAP5 solution.Accordingly, L-Trp
Addition the fluorescence of BTAP5 solution is quenched quickly, and the addition of remaining cation does not influence on the fluorescence of BTAP5 solution.
It is emphasized that BTAP5 only has 35s for L-Trp response time.
2nd, the titration experiments of the quaternized aromatic hydrocarbons of post 5 and L-Trp
Pipette 2.0mL BTAP5 DMSO (aqueous 70%) solution（2.0×10-4mol·L-1）In quartz cell, it is loaded with accumulation
Method is gradually added into the L-Trp aqueous solution, and its fluorescence emission spectrum is surveyed in 25 DEG C（Fig. 2）.Titration experiments explanation, BTAP5 fluorescence
Intensity is influenceed by L-Trp concentration, weakens along with the increase of L-Trp concentration.And obtained according to titration experiments
Detections of the BTAP5 to L-Trp fluorescence spectrum is limited to 2.83 × 10−7mol/L.Thus illustrate, BTAP5 energy single selectives are glimmering
Light recognizes L-Trp, and very high to L-Trp detection sensitivity, and therefore, BTAP5 has potential application in L-Trp context of detection
Value.
Fig. 3 is the L-Trp of various concentrations（0 ~ 3.0 times）In the presence of BTAP5 fitting a straight line figure.Fitting a straight line figure can be clear
Variation tendency of the clear clear reflection BTAP5 fluorescence intensity in 0 ~ 3.0 times of L-Trp concentration range.Pass through fitting a straight line figure
It can be found that L-Trp in 0 ~ 3.0 times of equivalent and BTAP5 fluorescence intensity in preferable linear relationship it is as follows：
Y=-187.7435X+759.19789；R2=0.9975
Wherein, Y --- BTAP5 fluorescence intensity, X --- L-Trp relative concentration.
3rd, the amino acid interference free performance detection of the quaternized aromatic hydrocarbons of post 5
In order to determine Detection results of the BTAP5 to L-Trp, we have carried out following test again：Take two groups of 10mL colorimetric cylinders difference
The 0.5 mL BTAP5 solution is added, then is separately added into the aqueous solution of the various amino acid of 2.5 mL（2×10-3mol·L−1）, plus steam
The mL of distilled water 1.0, is then diluted to 5 mL scales with dimethyl sulfoxide (DMSO).Add 2.5mL L-Trp in another set respectively again, every
1.0 mL β-Al, L-Arg, L-Cys, L-Gly, L-Lys, L-Pro, L-Met, L-Thr, L- are separately added into one colorimetric cylinder
Ser, L-His, L-Val, L-Tyr, L-Asn, L-Glu, L-Gln, L-Ile, L-Phe, DL-Asp, the L-Leu aqueous solution
（0.005mol·L-1）, 5mL scales are then diluted to dimethyl sulfoxide (DMSO).Observed after above-mentioned solution is well mixed.
Above-mentioned solution left standstill surveys its fluorescence emission spectrum after 25 DEG C.As a result find, add after above-mentioned 19 kinds of amino acid,
Only BTAP5 fluorescence at 330nm is quenched quickly, and this influence with L-Trp to BTAP5 is consistent.So as to illustrate such
BTAP5 compound tests L-Trp is not disturbed by other amino acid（See Fig. 4）.
Experiment shows, in BTAP5 aqueous dimethyl sulphoxide solution, and the percentage by volume of water is 60 ~ 80%, quaternized
The concentration of the aromatic hydrocarbons of post 5 is 2 × 10-5~4×10-5mol·L-1, BTAP5 can highly sensitive single selective fluorescence identifying L-
Trp, and L-Trp concentration and BTAP5 fluorescence intensity are in above-mentioned linear relationship.
4th, the quaternized aromatic hydrocarbons of post 5 detects L-Trp mechanism
The quaternized aromatic hydrocarbons of post 5 provides a good cavity structure, so the object with suitable construction size can be penetrated into
The result of host-guest inclusion is reached in its cavity；Post aromatic hydrocarbons after quaternized has good water solubility, and this is greatly solved
Main body recognizes in aqueous systems the puzzlement of amino acid.In addition, the fluorescence of the post aromatic hydrocarbons after quaternized is relatively strong, thus short
Recognition effect is reached to L-Trp in time.Therefore, L-Trp identification can be used for as new identification system.
Brief description of the drawings
Fluorescence spectrum when Fig. 1 is BTAP5 and adds 20 kinds of amino acid（Excitation wavelength：255nm, launch wavelength
330nm）.
Fig. 2 is the L-Trp of various concentrations（0 ~ 7.75 times）In the presence of BTAP5 fluorescence spectrum.
Fig. 3 is the L-Trp of various concentrations（0 ~ 3.0 times）In the presence of BTAP5 fitting a straight line figure.
Fig. 4 is the interference free performance that BTAP5 is recognized to L-Trp；1 ~ 20 represents BTAP5, β-Ala, L-Arg, L- respectively
Cys, L-Gly, L-Lys, L-Pro, L-Met, L-Thr, L-Ser, L-His, L-Val, L-Tyr, L-Asn, L-Glu, L-Gln,
L-Ile, L-Phe, DL-Asp and L-Leu.
Embodiment
BTAP5 of the present invention synthesis and fluoroscopic examination L-Trp application are done further below by specific embodiment
Explanation.
The synthesis of embodiment 1, the aromatic hydrocarbons of quaternized post 5
（1）The synthesis of the aromatic hydrocarbons of symmetry post 5
The synthesis of intermediate 1：By hydroquinones（2.2 g, 20.0 mmol）、K2CO3（13.8 g, 100 mmol）、KI（0.83
G, 5mmol）、PEG-400（4mL, 10mmol）, 1,4 dibromobutanes（17.28 g, 80mmol）And acetone（300~400mL）Plus
Enter into 500mL round-bottomed flasks, stirring reaction（36h）, room temperature is cooled to, suction filtration is removed after inorganic salts, the dry solvent of vacuum rotary steam,
Pillar layer separation, it is midbody compound 1 to obtain white solid.Yield is 80%；m.p: 83~85°C;1H NMR (400MHz,
CDCl3) δ(ppm): δ 6.81 (s, 4H), 3.94 (dd, J = 10.0, 5.8 Hz, 4H), 3.48 (t, J =
6.6 Hz, 2H), 3.26 (t, J = 6.8 Hz, 2H), 2.09-1.85 (m, 8H)。
The synthesis of the aromatic hydrocarbons 2 of symmetry post 5：By 1,2- dichloroethanes（300mL）It is added in 500mL circle low fever's bottles, at it
Middle addition midbody compound 1（1.9g, 5mmol）, terephthaldehyde's ether（2.76g, 20mmol）, paraformaldehyde（0.75g,
25mmol）BFEE（6.75mL（47%）, 25mmol）, 3 ~ 4h is reacted at room temperature, then with methanol extraction, chloroform extraction
Take, distilled water extraction, anhydrous sodium sulfate drying, organic phase pillar layer separation, it is the aromatic hydrocarbons 2 of symmetry post 5 to obtain white solid.
Yield: 34%；m.p: 187-189°C;1H NMR (600 MHz, CDCl3) δ 6.84 – 6.74 (m, 10H), 3.87
(t, J= 5.9 Hz, 4H), 3.83 – 3.78 (m, 10H), 3.72 (t, J= 19.9 Hz, 24H), 3.33 (s,
4H), 1.94 (s, 4H), 1.84 (s, 4H);ESI-MS m/z: (M+NH4)+ Calcd for
C51H64O10Br2N1010.2871; Found 1010.2878。
（2）The synthesis of the quaternized aromatic hydrocarbons of post 5：80mL ethanol is added in 500mL circle low fever's bottles, added wherein symmetrical
The property aromatic hydrocarbons 2 of post 5（0.5g, 0.5mmol）, trimethylamine（The ethanol solution of 33% volume, 1.0 mL, 3.7 mmol）, 78 DEG C of backflows
24h is reacted, room temperature is cooled to, the dry solvent of vacuum rotary steam obtains white solid, then is washed 2 ~ 3 times with ethanol, obtains white solid i.e.
For the quaternized aromatic hydrocarbons BTAP5 of post 5.Yield: 93%.m.p: 176−178 °C.1H NMR (600 MHz, D2O/DMSO-d 6
(4 : 1 , v/v)) δ 6.84 – 6.54 (m, 10H), 3.65 (s, 4H), 3.51 (dd, J= 23.6, 16.5
Hz, 18H), 3.23 (t, J= 24.3 Hz, 10H), 3.07 – 2.94 (m, 24H), 1.76 (d, J= 84.5
Hz, 12H); ESI−MS m/z: (M-2Br)2+ Calcd for C57H78O10N2 475.2823; Found 475.2828。
Its synthetic route is as follows：
Embodiment 2, with BTAP5 fluorescence identifyings L-Trp
In BTAP5 dimethyl sulphoxide solution（2×10-4mol·L-1）, it is separately added into L-Trp, β-Ala, L-Arg, L-
Cys, L-Gly, L-Lys, L-Pro, L-Met, L-Thr, L-Ser, L-His, L-Val, L-Tyr, L-Asn, L-Glu, L-Gln,
L-Ile, L-Phe, DL-Asp and the L-Leu aqueous solution（1×10-3mol·L-1）If the fluorescent quenching of BTAP5 solution is said
Bright addition is L-Trp, if the fluorescence of BTAP5 solution does not change, and that illustrate addition is not L-Trp.
Embodiment 3, with BTAP5 detect L-Trp concentration
In 4mL BTAP5 dimethyl sulphoxide solution（2×10-4mol·L-1）, the 1mL L-Trp aqueous solution is added, in 25 DEG C
Its fluorescence emission spectrum is surveyed, the fluorescence intensity of solution is 635.4.According to the fluorescence intensity of BTAP5 solution and L-Trp concentration
Linear relationship, calculates L-Trp concentration.
The linear relationship of the fluorescence intensity of BTAP5 solution and L-Trp concentration is as follows：
Y=-187.7435X+759.19789；R2=0.9975
Wherein, Y --- the fluorescence intensity of BTAP5 solution, X --- L-Trp relative concentration.
The concentration for calculating L-Trp solution is 1.3 × 10-4mol·L-1。
Claims (9)
1. the quaternized aromatic hydrocarbons of post 5, its structural formula is：
。
2. the synthetic method of the quaternized aromatic hydrocarbons of post 5 as claimed in claim 1, is, using ethanol as solvent, to make the virtue of symmetry copolymerization post 5
Hydrocarbon and trimethylamine back flow reaction；Reaction is cooled to room temperature after terminating, and the dry solvent of vacuum rotary steam, obtained white solid is washed with ethanol
Wash, produce the quaternized aromatic hydrocarbons of post 5.
3. the synthetic method of the quaternized aromatic hydrocarbons of post 5 as claimed in claim 2, it is characterised in that：The aromatic hydrocarbons of symmetry copolymerization post 5 and three
The mol ratio position 1 of methylamine:5~1:8.
4. the synthetic method of the quaternized aromatic hydrocarbons of post 5 as claimed in claim 2, it is characterised in that：Back flow reaction temperature is 78 DEG C, instead
It is 20 ~ 24h between seasonable.
5. the quaternized aromatic hydrocarbons fluoroscopic examination L-Trp of post 5 as claimed in claim 1.
6. the quaternized aromatic hydrocarbons of post 5 as claimed in claim 5 is used for fluoroscopic examination L-Trp, it is characterised in that：In quaternized post 5
In the aqueous dimethyl sulphoxide solution of aromatic hydrocarbons, L-Trp, β-Ala, L-Arg, L-Cys, L-Gly, L-Lys, L-Pro are separately added into,
L-Met, L-Thr, L-Ser, L-His, L-Val, L-Tyr, L-Asn, L-Glu, L-Gln, L-Ile, L-Phe, DL-Asp and L-
The addition of the Leu aqueous solution, only L-Trp can make the fluorescent quenching of the quaternized arene solution of post 5, and the addition of remaining cation
The fluorescence of the quaternized arene solution of post 5 is not influenceed.
7. the quaternized aromatic hydrocarbons of post 5 as claimed in claim 6 is used for fluoroscopic examination L-Trp, it is characterised in that：The quaternized virtue of post 5
The linear relationship of the fluorescence intensity of the aqueous dimethyl sulphoxide solution of hydrocarbon and L-Trp concentration is as follows：
Y=-187.7435X+759.19789；R2=0.9975
Wherein, Y --- the fluorescence intensity of the quaternized arene solution of post 5：Unit：a.u.
X --- L-Trp relative concentration, unit：mol/L.
8. the quaternized aromatic hydrocarbons of post 5 is used for fluoroscopic examination L-Trp as claimed in claims 6 or 7, it is characterised in that：Aqueous diformazan
In base sulfoxide solution, the percentage by volume of water is 60 ~ 80%.
9. the quaternized aromatic hydrocarbons of post 5 is used for fluoroscopic examination L-Trp as claimed in claims 6 or 7, it is characterised in that：Aqueous diformazan
In base sulfoxide solution, the concentration of the quaternized aromatic hydrocarbons of post 5 is 2 × 10-5~4×10-5mol·L-1。
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| CN112174883A (en) * | 2020-10-29 | 2021-01-05 | 西北师范大学 | Synthesis and application of fluorescent sensor capable of singly and selectively identifying L-arginine |
| CN112174883B (en) * | 2020-10-29 | 2022-05-03 | 西北师范大学 | Synthesis and application of fluorescent sensor capable of singly and selectively identifying L-arginine |
| CN112362628A (en) * | 2020-11-12 | 2021-02-12 | 贵州师范学院 | Fluorescent probe for detecting L-tryptophan |
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Application publication date: 20170829 |