CN1825107A - Method for detecting chiral isomer - Google Patents
Method for detecting chiral isomer Download PDFInfo
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- CN1825107A CN1825107A CN 200610025489 CN200610025489A CN1825107A CN 1825107 A CN1825107 A CN 1825107A CN 200610025489 CN200610025489 CN 200610025489 CN 200610025489 A CN200610025489 A CN 200610025489A CN 1825107 A CN1825107 A CN 1825107A
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Abstract
The invention relates to a method to detect chirality isomer. It uses BSA as chirality choosing agent to identify isomer sample marked by metal nm particle and taking the method of electrochemistry to realize chirality identification. The sensor could high effectively test chirality amino acid and drugs. Experiment shows, the chirality sensor could detect 0.1pico mol thickness amino acid isomer.
Description
Technical field
The present invention relates to nanometer technology, biotechnology and electrochemical research field particularly, the invention provides a kind of method that detects chiral isomer.
Background technology
Chipal compounds and life process are closely bound up, different chiral isomers biologically active in vivo, pharmacological action, metabolic processes etc. have tangible difference, therefore development is simple, and accurately, the chiral Recognition method becomes the main direction of chiral analysis in recent years fast.Recent years, the research of chiral sensor has obtained certain development, chiral selector major part wherein is the chiral stationary phase (A.Tsourkas that uses for reference on the chromatogram, 0.Hofstetter, H.Hofstetter, R.Weissleder, L.Josephson, Angew.Chem.Int.Edit.2004,43,2395).Albumen is owing to have complicated and reversible conformation, separating chiral isomeride well on chromatogram, and domestic existing patent (number of patent application: 99113091.X, publication number: CN 1280986A) report utilizes albumen to make the chromatogram chiral stationary phase.For example BSA is used to separating chiral amino acid and chiral drug usually on chromatogram, separating effect is fine, and experiment and structure analysis prove that the chiral selectivity of BSA is mainly derived from its stereoselectivity between chipal compounds (host-guest), hydrogen bond action and hydrophilic and hydrophobic (M.Kato, K.Sakai-Kato, N.Matsumoto, T.Toyo ' oka, Anal.Chem.2002,74,1915; C.V.Kumar, A.Buranaprapuk, H.C.Sze, Chem.Comm.2001,3,297), yet up to the present, the BSA chiral Recognition of on chiral sensor, carrying out also of no use.Therefore, the advantage that can simply, fast and accurately measure analyte with good chiral selectivity of BSA and sensor is integrated as point of penetration, will have important theory and practical study meaning to the development of chiral sensor.
On the other hand, nano material is considered to the focus in cross-centennial investigation of materials field.The quantum size effect of nano material itself, small-size effect and surface effect etc. make it have many distinctive character, therefore are widely used at aspects such as catalysis, biological medicine and new materials.Synthetic (the P.Selvakannan of the aqueous metal nano particle of bibliographical information wherein, S.Mandal, S.Phadtare, A.Gole, R.Pasricha, S.D.Adyanthaya, M.Sastry, J.Colloid.Interf.Sci.2004,269,97), opened up wide prospect in the application (biological example mark and drug conveying) of biological field for nano material.For the chiral sensor of albumen as chiral selector, metal nanoparticle can be used for mark chiral amino acid isomeride, thereby detect the chiral Recognition result by the Electrochemical Detection metal nanoparticle.
Summary of the invention
The purpose of this invention is to provide a kind of method that detects chiral isomer.
The invention provides a kind of method that detects chiral isomer.The sensor that is about to contain bovine serum albumin(BSA) places the phosphate buffer solution of the chiral isomer testing sample that contains the metal nanoparticle mark, hatches 8-12 minute, and the pH scope of phosphate buffer solution is 6-9; After the hatching, fully wash electrode, carry out electrochemical gaging then and get final product with distilled water.
The above-mentioned sensor that contains bovine serum albumin(BSA), this sensor electrode surface coverage contains the alumina sol-gel mould of bovine serum albumin(BSA), and the thickness range of film is 20～40nm.
Experimental result shows that this sensor is chiral Recognition effectively, and can detect amino acid isomeride and medicine isomeride delicately.
In the sensor of the present invention, electrode can be screen printing electrode or glass-carbon electrode etc.
Sensor of the present invention prepares as follows: being about to concentration is 0.05-0.2mg mL
-1Bovine serum albumin(BSA) and alumina sol-gel mix, the volume ratio of bovine serum albumin(BSA) and alumina sol-gel is 0.5: 1-1.2: 1; Mixed solution covers on the electrode, and 0-4 ℃ leaves standstill curing 60-80 hour; At last the above-mentioned electrode that makes is connected with electrochemical appliance, makes sensor.
In the sensor preparation process of the present invention, the concentration of used bovine serum albumin(BSA) is 0.09-0.15mg mL
-1The time, the result more optimizes.
In the sensor preparation process of the present invention, used electrode can be screen printing electrode or glass-carbon electrode etc.
Sensor of the present invention is in preparation process, and used sensor electrode can be shaft-like glass-carbon electrode, and its diameter can be the 2-4 millimeter.
This sensor mainly be by alumina sol-gel under cryogenic conditions fixedly BSA prepare sensor, the preparation method is simple, it is good that protein active keeps.During chiral Recognition, only need the amino acid isomeride solution of this sensor and metal nanoparticle mark was hatched respectively 8-12 minute, then obtain the chiral Recognition result by Electrochemical Detection, simple to operate, save time, and have higher detection sensitivity.
In the method for the present invention, adopting metal nanoparticle can be gold grain, elargol particle, Ag@Au or Cu@Au alloy nanoparticle, etc.
In the method for the present invention, the testing sample isomeride of employing is tryptophane isomeride, benzo propylhomoserin isomeride or tyrosine isomeride, also can be chiral drug etc.
In the method for the present invention, metal nanoparticle can be a gold size, behind gold label silver stain, comes the oxidation signal of Electrochemical Detection silver; Can be elargol and nano copper sulfate particle etc. also, directly detect metal nanoparticle.The object of chiral Recognition can be the tryptophane isomeride, also can be the benzo propylhomoserin, tyrosine and some chiral drugs.
In the method for the present invention, adopt three-electrode system to carry out electrochemical gaging, platinum filament is to electrode, and saturated calomel electrode is a contrast electrode, and sensor electrode after the chiral Recognition or carbon fiber electrically be working electrode very, at 0.08-0.12mol L
-1Acetate type buffer solution (pH 4.8-5.5) or 0.08-0.12mol L
-1In the liquid, write down the differential pulse voltammetry curve at the bottom of the nitric acid.
The invention provides a kind of method that detects chiral isomer.A kind of method detection sensitivity that detects chiral isomer of the present invention can be applied to detect and separating chiral amino acid and chiral drug than higher efficiently.Experiment shows that this method can detect the amino acid isomeride of 0.1 picomole concentration.
Description of drawings
Fig. 1 is a chiral Recognition process synoptic diagram.
Fig. 2 is the figure as a result of chirality tryptophane identification.On behalf of this sensor, curve a and b L-and D-tryptophane are carried out the result of chiral Recognition respectively.Definition isomery selectivity factor α discerns the ratio of the oxidation peak current of gained silver to L-and D-type amino acid for this sensor.Then this sensor is 2.3 to the isomery selectivity factor of tryptophane.Experimental result shows that this sensor reaches 0.1 picomole concentration to the detectability of tryptophane isomeride.
Fig. 3 is the peak current of this sensor and isomery selectivity factor with tryptophane isomeride concentration change figure as a result.
Embodiment
Come below by the tryptophane isomeride of this sensor identification gold size mark that the present invention is described further.
(1) preparation of gold size
HAuCl with 500mL 1mM
4Solution is heated to and boils, and adds the citric acid three sodium solution of 50mL 38.8mM again, continues ebuillition of heated 10min, stops heated and stirred again 15 minutes, promptly makes the gold size that diameter is about 13-15nm, with being placed on brown bottle 0-4 ℃ preservation behind the 0.22m membrane filtration.
(2) preparation of the tryptophane isomeride of gold size mark
Respectively the tryptophane isomeride solution of 1mL0.01mM concentration is joined above the 9mL in the freshly prepd gold size solution room temperature 20-30 ℃ of assembling 48 hours.
(3) sensor preparation
With 0.1mg mL
-1BSA and alumina sol-gel mixed solution 5 μ L (1: 1v/v) drip on glass-carbon electrode (Φ=4), leave standstill at 0-4 ℃ and solidified 72 hours, the alumina sol of formation-gel mould thickness is 25 ± 3nm.
(4) chiral Recognition
Tryptophane isomeride solution with the gold size mark of 10L step (2) preparation joins in the 10mL phosphate buffer solution (pH:7) respectively, then two sensors are hatched 10 minutes respectively therein after, fully wash with distilled water.
(5) gold label silver stain
Place silver to dye solution (mixed solution of the citrate buffer solution solution (pH=3.8) of the liquor argenti nitratis ophthalmicus of 150 μ L0.22% and 150 μ L1% p-dihydroxy-benzene) lucifuge reaction 8 minutes respectively two sensors after the chiral Recognition, after fully washing with distilled water, then at 2.5%Na
2S
2O
3Aqueous solution placed 3 minutes, fully wash with distilled water more at last.
(6) electrochemical gaging
Adopt three-electrode system, platinum filament is to electrode, and saturated calomel electrode is a contrast electrode, and the glass-carbon electrode after silver dyes is a working electrode, and the acetic acid of 0.1mol/L-sodium acetate buffer solution (pH 5.2) is end liquid, record differential pulse voltammetry (DPV) curve.Sweep limit: 0.1V-0.8V (vs SCE).Wherein contrast electrode is isolated itself and end liquid with two salt bridges, avoids the Cl that constantly discharges
-Form AgCl precipitation interference measurement with silver.
This chiral sensor carries out the chiral Recognition tryptophane according to above-mentioned embodiment, and the chiral Recognition process is shown in Figure 1, and the chiral Recognition result who obtains as shown in Figures 2 and 3.In Fig. 2, on behalf of this sensor, curve a and b L-and D-tryptophane are carried out the result of chiral Recognition respectively.Definition isomery selectivity factor α discerns the ratio of the oxidation peak current of gained silver to L-and D-type amino acid for this sensor.Then this sensor is 2.3 to the isomery selectivity factor of tryptophane.Experimental result shows that this sensor reaches 0.1 picomole concentration to the detectability of tryptophane isomeride.Fig. 3 represents this sensor with tryptophane isomeride concentration change, the situation of change of the peak current of its detection and isomery selectivity factor.
Come below by the benzo propylhomoserin isomeride of this sensor identification gold size mark that the present invention is described further.
(1) preparation of the phenylalanine of the preparation of gold size and gold size mark is with embodiment 1
(2) sensor preparation
With 0.1mg mL
-1BSA and alumina sol-gel mixed solution 10 μ L (1: 1v/v) drip that (on the Φ=2mm), leave standstill at 0-4 ℃ and to solidify 72 hours, the alumina sol of formation-gel mould thickness is 31 ± 2nm at glass-carbon electrode.
(3) chiral Recognition
Isomers of phenylalanine solution with the gold size mark of 10L step (2) preparation joins in the 10mL phosphate buffer solution (pH:7.4) respectively, then two sensors are hatched 11 minutes respectively therein after, fully wash with distilled water.
(4) gold label silver stain
Place silver to dye solution (mixed solution of the citrate buffer solution solution (pH=3.8) of the liquor argenti nitratis ophthalmicus of 150 μ L0.22% and 150 μ L1% p-dihydroxy-benzene) lucifuge reaction 8.5 minutes respectively two sensors after the chiral Recognition, after fully washing with distilled water, then at 2.5%Na
2S
2O
3Aqueous solution placed 3 minutes, fully wash with distilled water more at last.
(5) electrochemical determination method is with embodiment 1
This chiral sensor carries out chiral Recognition with above-mentioned embodiment to isomers of phenylalanine, and the isomery selectivity factor that obtains is 1.3.
Come below by the tyrosine isomeride of this sensor identification gold size mark that the present invention is described further.
(1) preparation of the phenylalanine of the preparation of the preparation gold size of gold size and gold size mark is with embodiment 1
(2) sensor preparation
With 0.1mg mL
-1BSA and alumina sol-gel mixed solution 15 μ L (1: 1v/v) drip on glass-carbon electrode (Φ=4), leave standstill at 0-4 ℃ and solidified 72 hours, the alumina sol of formation-gel mould thickness is 36 ± 2nm.
(3) chiral Recognition
Tyrosine isomeride solution with the gold size mark of 10L step (2) preparation joins in the 10mL phosphate buffer solution (pH:8) respectively, then two sensors are hatched 12 minutes respectively therein after, fully wash with distilled water.
(4) gold label silver stain
Place silver to dye solution (mixed solution of the citrate buffer solution solution (pH=3.8) of the liquor argenti nitratis ophthalmicus of 150 μ L 0.22% and 150 μ L, 1% p-dihydroxy-benzene) lucifuge reaction 9 minutes respectively two sensors after the chiral Recognition, after fully washing with distilled water, then at 2.5%Na
2S
2O
3Aqueous solution placed 3 minutes, fully wash with distilled water more at last.
(5) electrochemical determination method is with embodiment 1
This chiral sensor carries out chiral Recognition tyrosine according to above-mentioned embodiment, and the isomery selectivity factor that obtains is 1.36.
Embodiment 4
Come below by the tryptophane isomeride of this sensor identification elargol mark that the present invention is described further.
(1) preparation of elargol
At 10mL 10
-3Mol L
-1AgNO
3In the solution, slowly drip 10mL 3 * 10
-3Mol L
-1NaBH
4Be reflected to stir in the ice bath and carry out, after dripping, leave ice bath, the stirring that does not stop is increased to room temperature gradually until solution temperature, the light yellow colloid of the clear that obtains, then with this colloid dialysis purification 24h in semi-permeable diaphragm, the pale brown look elargol that obtains, the nanometer elargol that promptly will prepare, its footpath grain is distributed within the 20-25nm scope.
(2) preparation of the tryptophane isomeride of elargol mark
Respectively the tryptophane isomeride solution of 1mL0.01mM concentration is joined above the 9mL in the freshly prepd fulmargin room temperature 20-30 ℃ of assembling 48 hours.
(3) sensor preparation
With 0.1mg mL
-1BSA and alumina sol-gel mixed solution 5 μ L (1: 1v/v) drip on glass-carbon electrode (Φ=4), leave standstill at 0-4 ℃ and solidified 72 hours.
(4) chiral Recognition
Tryptophane isomeride solution with the elargol mark of 10L step (2) preparation joins in the 10mL0.01M phosphate buffer solution (pH:7) respectively, then two sensors are hatched 8 minutes respectively therein after, fully wash with distilled water.
(5) Yin oxidation dissolution
Two sensors finishing the chiral Recognition reaction are immersed the HNO of 150L 50% respectively
3In the solution, vibration makes silver-colored oxidation dissolution, takes out sensor behind the 5min, and adds 0.8mL 10mM HNO
3-KNO
3Solution carries out Electrochemical Detection as supporting electrolyte in this solution
(6) electrochemical gaging
Adopt three-electrode system, platinum filament is to electrode, and saturated calomel electrode is a contrast electrode, and the 5m carbon fiber microelectrodes with micro pipette tips is a working electrode, in above-mentioned solution, adopts Anodic Stripping Voltammetry Determination Ag
+Electrode under-0.5V behind the preenrichment 150s, 0.0～+ the 0.6V scope in oppositely stripping, record stripping DPV signal.Wherein contrast electrode is isolated itself and end liquid with two salt bridges, avoids the Cl that constantly discharges
-Form AgCl precipitation interference measurement with silver.
Embodiment 5
Come below by the benzo propylhomoserin isomeride of this sensor identification elargol mark that the present invention is described further.
(1) preparation of the isomers of phenylalanine of the preparation of elargol and elargol mark is with embodiment 1
(2) sensor preparation
With 0.1mg mL
-1BSA and alumina sol-gel mixed solution 10 μ L (1: 1v/v) drip on glass-carbon electrode (Φ=3), leave standstill at 0-4 ℃ and solidified 72 hours.
(4) chiral Recognition
Tryptophane isomeride solution with the gold size mark of 15L step (2) preparation joins in the 10mL0.02M phosphate buffer solution (pH:8) respectively, then two sensors are hatched 10 minutes respectively therein after, fully wash with distilled water.
(5) Yin oxidation dissolution
Two sensors finishing the chiral Recognition reaction are immersed the HNO of 200L 50% respectively
3In the solution, vibration makes silver-colored oxidation dissolution, takes out glass-carbon electrode behind the 5min, and adds 1mL 10mMHNO
3-KNO
3Solution carries out Electrochemical Detection as supporting electrolyte in this solution
(6) electrochemical determination method is with embodiment 4.
Claims (4)
1. method that detects chiral isomer, it is characterized in that, the sensor that will contain bovine serum albumin(BSA) places the phosphate buffer solution of the chiral isomer testing sample that contains the metal nanoparticle mark, hatches 8-12 minute, and the pH scope of phosphate buffer solution is 6-9; After the hatching, fully wash electrode, carry out electrochemical gaging then and get final product with distilled water.
2. the method for claim 1 is characterized in that, metal nanoparticle is gold grain, elargol particle, gold and silver or copper-gold alloy nano particle.
3. the method for claim 1 is characterized in that, the testing sample isomeride is tryptophane isomeride, benzo propylhomoserin isomeride or tyrosine isomeride.
4. the method for claim 1 is characterized in that, adopts three-electrode system to carry out electrochemical gaging, platinum filament is to electrode, saturated calomel electrode is a contrast electrode, and sensor electrode after the chiral Recognition or carbon fiber electrically be working electrode very, at the 0.08-0.12mol of pH 4.8-5.5 L
-1Acetate type buffer solution or 0.08-0.12mol L
-1In the liquid, write down the differential pulse voltammetry curve at the bottom of the nitric acid.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104792844A (en) * | 2015-04-01 | 2015-07-22 | 常州大学 | Preparation of chitosan-carbon quantum dot composite film modified electrode and application of chitosan-carbon quantum dot composite film modified electrode to electrochemical identification of tryptophan enantiomer |
| CN105067686A (en) * | 2015-07-23 | 2015-11-18 | 常州大学 | Selectivity identification of poly L-glutamic acid/amylose-modified glassy carbon electrode on tryptophan enantiomer |
| CN106770569A (en) * | 2016-12-01 | 2017-05-31 | 山西大学 | A kind of application of gold nano of N acetyl L cysteines protection and application process |
| CN108445064A (en) * | 2018-03-05 | 2018-08-24 | 常州大学 | A kind of preparation method of the graphene quantum dot can be applied to electrochemistry chiral Recognition-bovine serum albumin(BSA) composite material |
| CN112326760A (en) * | 2020-10-22 | 2021-02-05 | 天津大学 | Preparation and detection method of epitaxial gate field effect transistor sensor for detecting chiral tryptophan |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5198367A (en) * | 1989-06-09 | 1993-03-30 | Masuo Aizawa | Homogeneous amperometric immunoassay |
| CN1055933C (en) * | 1995-05-09 | 2000-08-30 | 中国科学院上海有机化学研究所 | Polyclonal antibody, preparing process and use thereof |
| JP3539026B2 (en) * | 1995-12-08 | 2004-06-14 | Ｎｏｋ株式会社 | Urine sugar biosensor |
| CN1200275C (en) * | 2001-01-12 | 2005-05-04 | 吉林大学 | Electrode modified by chiral material with nm pores |
| CN1696683A (en) * | 2005-06-17 | 2005-11-16 | 武汉科技大学 | Uricase biosensor and preparation method |
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2006
- 2006-04-06 CN CNB2006100254893A patent/CN100439914C/en not_active Expired - Fee Related
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104792844A (en) * | 2015-04-01 | 2015-07-22 | 常州大学 | Preparation of chitosan-carbon quantum dot composite film modified electrode and application of chitosan-carbon quantum dot composite film modified electrode to electrochemical identification of tryptophan enantiomer |
| CN104792844B (en) * | 2015-04-01 | 2018-02-02 | 常州大学 | The preparation of a kind of complex film modified electrode of chitosan carbon quantum dot and its applied to electrochemical recognition Tryptophan enantiomer |
| CN105067686A (en) * | 2015-07-23 | 2015-11-18 | 常州大学 | Selectivity identification of poly L-glutamic acid/amylose-modified glassy carbon electrode on tryptophan enantiomer |
| CN105067686B (en) * | 2015-07-23 | 2017-09-08 | 常州大学 | The Selective recognition of poly- L glutamic acid/amylose modified glassy carbon electrode tryptophan enantiomer |
| CN106770569A (en) * | 2016-12-01 | 2017-05-31 | 山西大学 | A kind of application of gold nano of N acetyl L cysteines protection and application process |
| CN108445064A (en) * | 2018-03-05 | 2018-08-24 | 常州大学 | A kind of preparation method of the graphene quantum dot can be applied to electrochemistry chiral Recognition-bovine serum albumin(BSA) composite material |
| CN112326760A (en) * | 2020-10-22 | 2021-02-05 | 天津大学 | Preparation and detection method of epitaxial gate field effect transistor sensor for detecting chiral tryptophan |
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