CN107102051B - A kind of application of the phenylalanine dipeptide self assembly product of iron ion induction in electrochemistry chiral Recognition field - Google Patents
A kind of application of the phenylalanine dipeptide self assembly product of iron ion induction in electrochemistry chiral Recognition field Download PDFInfo
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- CN107102051B CN107102051B CN201710134983.1A CN201710134983A CN107102051B CN 107102051 B CN107102051 B CN 107102051B CN 201710134983 A CN201710134983 A CN 201710134983A CN 107102051 B CN107102051 B CN 107102051B
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- 108010016626 Dipeptides Proteins 0.000 title claims abstract description 71
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 title claims abstract description 71
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 title claims abstract description 70
- 238000001338 self-assembly Methods 0.000 title claims abstract description 51
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 229910052742 iron Inorganic materials 0.000 title claims abstract description 44
- 230000006698 induction Effects 0.000 title claims abstract description 41
- 230000005518 electrochemistry Effects 0.000 title claims abstract description 10
- 238000005557 chiral recognition Methods 0.000 title claims abstract description 9
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical class C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims abstract description 4
- -1 iron ion Chemical class 0.000 claims description 38
- 230000000694 effects Effects 0.000 claims description 11
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical class FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims description 7
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims description 5
- 229910001447 ferric ion Inorganic materials 0.000 claims description 5
- 229910021397 glassy carbon Inorganic materials 0.000 claims description 4
- 229910000403 monosodium phosphate Inorganic materials 0.000 claims description 4
- 235000019799 monosodium phosphate Nutrition 0.000 claims description 4
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 4
- 229910021642 ultra pure water Inorganic materials 0.000 claims description 4
- 239000012498 ultrapure water Substances 0.000 claims description 4
- 238000002484 cyclic voltammetry Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 7
- 150000001413 amino acids Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000013507 mapping Methods 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- DWNBOPVKNPVNQG-LURJTMIESA-N (2s)-4-hydroxy-2-(propylamino)butanoic acid Chemical compound CCCN[C@H](C(O)=O)CCO DWNBOPVKNPVNQG-LURJTMIESA-N 0.000 description 2
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropyl alcohol Natural products CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 230000009881 electrostatic interaction Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- YKHQSWIVNHQJSW-UHFFFAOYSA-N iron;oxalonitrile Chemical compound [Fe].N#CC#N YKHQSWIVNHQJSW-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 108010050939 thrombocytin Proteins 0.000 description 1
Classifications
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/416—Systems
- G01N27/48—Systems using polarography, i.e. measuring changes in current under a slowly-varying voltage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Electrochemistry (AREA)
- Analytical Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biophysics (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Abstract
Application the present invention relates to a kind of phenylalanine dipeptide self assembly product of iron ion induction in electrochemistry chiral Recognition field.The following steps are included: preparing the phenylalanine dipeptide self assembly product of iron ion induction, the phenylalanine dipeptide self assembly product modified electrode for preparing iron ion induction, electrochemical process identification Tryptophan enantiomer.The beneficial effects of the present invention are: the phenylalanine dipeptide self assembly product modified electrode tryptophan enantiomer of iron ion induction has preferable recognition capability.This is because phenylalanine dipeptide has certain chiral environment.
Description
Technical field
The present invention relates to a kind of phenylalanine dipeptide self assembly products of iron ion induction in electrochemistry chiral Recognition field
Application, belong to biotechnology and electrochemical research field.
Technical background
Protein is the material base of life, is the basic organic matter for constituting cell, is the main undertaker of vital movement,
And amino acid is the basic composition unit of protein.Therefore, the separation of amino acid enantiomer is analyzed and researched to life science, drug
Chemistry, human health all have extremely important effect.Big amino acids all have chiral isomer, D- type and L-type enantiomer
Physiological action it is completely different.The intracorporal natural L-form amino acid of people can participate in the synthesis of protein, and D- type amino acid does not have
It is active or be harmful to the human body.Tryptophan is one of amino acid needed by human, has been identified as thrombocytin neurotransmitter
Presoma, therefore it accurately identified using technology appropriate, separated and purification seems of crucial importance.
So far, the height that the superior function of self-assembled material especially self-assembling peptide material causes numerous researchers is closed
Note.Among these, phenylalanine dipeptide self-assembled material relies on its distinctive property and foreseeable broad application prospect
Become the hot spot in research hotspot.
It is well known that metal ion is widely used as additive, adjusted by metal ligand coordination or electrostatic interaction
Structure.This item work with zinc ion come induce phenylalanine dipeptide carry out self assembly.The ligancy of zinc ion is 4, coordination ability
It is weaker.Zinc ion can be combined by coordinate bond and electrostatic interaction and electronegative phenylalanine dipeptide (in the case of pH=7), from
And phenylalanine dipeptide is induced to carry out self assembly, show different patterns.
Summary of the invention
The purpose of the invention is to provide a kind of phenylalanine dipeptide self assembly products of iron ion induction in electrochemistry
The application in chiral Recognition field.The phenylalanine dipeptide self assembly product of iron ion induction is modified after glass-carbon electrode can be high
The identification Tryptophan enantiomer of effect.
A kind of phenylalanine dipeptide self assembly product of iron ion induction of the present invention is in electrochemistry chiral Recognition field
Application, comprising the following steps:
A, it prepares the phenylalanine dipeptide self assembly product of iron ion induction: 1mg phenylpropyl alcohol is added in 20 μ L hexafluoroisopropanols
In propylhomoserin dipeptides, it is made into the hexafluoroisopropanol solution of 50mg/mL phenylalanine dipeptide, ultrapure water is added in Xiang Shangshu solution, it is dilute
It is interpreted into the phenylalanine dipeptide solution of 3mg/mL.Then ferric ion solutions are added into phenylalanine dipeptide solution, obtain iron ion
The phenylalanine dipeptide self assembly product of induction.
B, the phenylalanine dipeptide self assembly product modified electrode of iron ion induction is prepared: with liquid-transfering gun removing step a system
The phenylalanine dipeptide self assembly product of standby iron ion induction is added dropwise to glassy carbon electrode surface, at a certain temperature self assembly one
It fixes time, can be obtained the phenylalanine dipeptide self assembly product modified electrode of corresponding iron ion induction.
C, electrochemical process identifies Tryptophan enantiomer: Tryptophan enantiomer is identified using differential pulse method, by iron ion
After the phenylalanine dipeptide self assembly product modified electrode of induction rests in 20~30mL Tryptophan enantiomer solution, 0.4
Within the scope of the electrochemical window of~1.2V (vs.SCE) carry out differential pulse, surveyed every time after modified electrode 20~30mL 0.1~
It is swept in 0.3M sodium dihydrogen phosphate (pH=6~8) surely to restore electrode activity.
Further, the concentration of ferric ion solutions is 0.001~0.01mM in step a.
Further, the volume for the ferric ion solutions being added in step a is 10~30 μ L.
Further, the volume of the phenylalanine dipeptide solution for the iron ion induction that liquid-transfering gun pipettes in step b is 1~10
μL。
Further, 10~40 DEG C of self assembly temperature in step b.
Further, the self assembly time 4~8 hours in step b.
Further, the concentration of Tryptophan enantiomer is 0.1~1mM in step c.
Further, time of repose is 100~150 seconds in step c.
The beneficial effects of the present invention are: the phenylalanine dipeptide self assembly product modified electrode tryptophan of iron ion induction
Enantiomer has preferable recognition capability.This is because phenylalanine dipeptide has certain chiral environment.
Detailed description of the invention
This experiment is further illustrated with reference to the accompanying drawing.
Fig. 1 is the phenylalanine dipeptide self assembly product modified electrode tryptophan mapping of iron ion induction in embodiment one
The cyclic voltammogram of body identification.
Fig. 2 is the phenylalanine dipeptide self assembly product modified electrode tryptophan mapping of iron ion induction in embodiment two
The recognition effect figure of body.
Fig. 3 is the recognition effect figure of phenylalanine dipeptide modified electrode tryptophan enantiomer in comparative example one.A: iron from
The phenylalanine dipeptide self assembly product modified electrode of son induction；B: phenylalanine dipeptide modified electrode.
Fig. 4 is the field emission scanning electron microscope figure of phenylalanine dipeptide modified electrode in comparative example one.
Specific embodiment
Presently in connection with specific embodiment, the present invention will be further described, following embodiment be intended to illustrate invention rather than
Limitation of the invention further.
A kind of phenylalanine dipeptide self assembly product modified electrode tryptophan mapping of iron ion induction of the present invention
Body is identified as follows:
Δ E=EL-ED
In formula, Δ E indicates Tryptophan enantiomer oxidation peak potential difference, ELAnd EDRespectively indicate L-Trp and D- color ammonia
Acid oxidase spike potential value.
Embodiment one:
(1) it prepares the phenylalanine dipeptide self assembly product of iron ion induction: 1mg phenylpropyl alcohol is added in 20 μ L hexafluoroisopropanols
In propylhomoserin dipeptides, it is made into the hexafluoroisopropanol solution of 50mg/mL phenylalanine dipeptide, ultrapure water is added in Xiang Shangshu solution, it is dilute
It is interpreted into the phenylalanine dipeptide self assembly product of 3mg/mL.Then it is molten that 20 μ L iron ions are added into phenylalanine dipeptide solution
Liquid obtains the phenylalanine dipeptide self assembly product of iron ion induction.
(2) it prepares the phenylalanine dipeptide self assembly product modified electrode of iron ion induction: pipetting 5 μ L steps with liquid-transfering gun
(1) the phenylalanine dipeptide self assembly product of the iron ion induction prepared is added dropwise to glassy carbon electrode surface, the self assembly 6 at 30 DEG C
Hour, it can be obtained the phenylalanine dipeptide self assembly product modified electrode of corresponding iron ion induction.
(3) the phenylalanine dipeptide self assembly product modified electrode for the iron ion induction being prepared rests on 5mM iron cyanogen
Change in potassium solution, table is carried out to the modified electrode using cyclic voltammetry under the electrochemical window of -0.2~0.6V (vs.SCE)
Sign, sweeping speed is 0.1V/ seconds, and scanning circle number is 20 circles, and result is as shown in Fig. 1.
Embodiment two:
The phenylalanine dipeptide self assembly product modified electrode of the iron ion being prepared in embodiment one induction is stood
In 25mL Tryptophan enantiomer solution after 120 seconds, difference arteries and veins is carried out within the scope of the electrochemical window of 0.4~1.2V (vs.SCE)
Punching characterization, modified electrode is swept surely in 25mL 0.1M sodium dihydrogen phosphate (pH=7) to restore electrode activity after having surveyed every time.Iron
Recognition effect figure such as 2 institute of attached drawing of the phenylalanine dipeptide self assembly product modified electrode tryptophan enantiomer of ion induction
Show, the phenylalanine dipeptide self assembly product modified electrode tryptophan enantiomer of iron ion induction has preferable recognition effect
(Δ E is 72mV).
Comparative example one:
Phenylalanine dipeptide modified electrode electrochemical process identifies Tryptophan enantiomer including the following steps:
(1) 20 μ L hexafluoroisopropanols are added in 1mg phenylalanine dipeptide, are made into the six of 50mg/mL phenylalanine dipeptide
Ultrapure water is added in Xiang Shangshu solution in fluorine aqueous isopropanol, dilute 3mg/mL phenylalanine dipeptide solution.It is moved with liquid-transfering gun
5 μ L-Phe, two peptide solution is taken to be added dropwise to glassy carbon electrode surface, self assembly 6 hours at 30 DEG C can be obtained phenylalanine two
Peptide modified electrode.
(2) the phenylalanine dipeptide modified electrode prepared in step (1) is rested in 25mL L/D- tryptophan solution
After 120 seconds, difference arteries and veins characterization is carried out within the scope of the electrochemical window of 0.4~1.2V (vs.SCE), modification electricity after having surveyed every time
It is swept in 25mL 0.1M sodium dihydrogen phosphate (pH=7) surely to restore electrode activity pole.As shown in Fig. 3, phenylalanine dipeptide is repaired
The recognition effect figure (Δ E is 44mV) for adoring electrode tryptophan enantiomer is less desirable, this is because phenylalanine dipeptide exists
The phenomenon that electrode surface is reunited is more obvious, to be unfavorable for tryptophan modules into its chiral environment.Phenylalanine dipeptide is repaired
The field emission scanning electron microscope figure for adoring electrode is as shown in Fig. 4.
Claims (4)
1. a kind of application of phenylalanine dipeptide self assembly product of iron ion induction in electrochemistry chiral Recognition field, feature
Be: steps are as follows:
A, it prepares the phenylalanine dipeptide self assembly product of iron ion induction: 1mg phenylalanine is added in 20 μ L hexafluoroisopropanols
In dipeptides, it is made into the hexafluoroisopropanol solution of 50mg/mL phenylalanine dipeptide, ultrapure water is added in Xiang Shangshu solution, is diluted to
The phenylalanine dipeptide solution of 3mg/mL, is then added ferric ion solutions into phenylalanine dipeptide solution, obtains iron ion induction
Phenylalanine dipeptide self assembly product；
B, the phenylalanine dipeptide self assembly product modified electrode of iron ion induction is prepared: with liquid-transfering gun removing step a preparation
The phenylalanine dipeptide self assembly product of iron ion induction is added dropwise to glassy carbon electrode surface, one timing of self assembly at a certain temperature
Between, it can be obtained the phenylalanine dipeptide self assembly product modified electrode of corresponding iron ion induction；
C, electrochemical process identifies Tryptophan enantiomer: identifying Tryptophan enantiomer using differential pulse method, iron ion is induced
Phenylalanine dipeptide self assembly product modified electrode rest in 20~30mL Tryptophan enantiomer solution after, 0.4~
Differential pulse is carried out within the scope of the electrochemical window of 1.2V, modified electrode is in 20~30mL, 0.1~0.3M pH after having surveyed every time
To be swept surely with cyclic voltammetry to restore electrode activity in 6~8 sodium dihydrogen phosphate.
2. a kind of phenylalanine dipeptide self assembly product of iron ion induction is in electrochemistry chiral Recognition according to claim 1
The application in field, it is characterized in that: the concentration of ferric ion solutions is 0.001~0.01mM in the step a, the iron ion of addition is molten
The volume of liquid is 10~30 μ L.
3. a kind of phenylalanine dipeptide self assembly product of iron ion induction is in electrochemistry chiral Recognition according to claim 1
The application in field, it is characterized in that: the volume of the phenylalanine dipeptide solution for the iron ion induction that liquid-transfering gun pipettes in the step b
For 1~10 μ L, 10~40 DEG C of self assembly temperature, the self assembly time 4~8 hours.
4. a kind of phenylalanine dipeptide self assembly product of iron ion induction is in electrochemistry chiral Recognition according to claim 1
The application in field, it is characterized in that: in the step c Tryptophan enantiomer concentration be 0.1~1mM, time of repose be 100~
150 seconds.
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| CN114152655B (en) * | 2021-12-31 | 2023-11-14 | 常州大学 | Polystyrene and L-Phe compound modified electrode for chiral recognition of glutamic acid enantiomer and preparation method thereof |
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|---|---|---|---|---|
| CN102466659A (en) * | 2010-11-15 | 2012-05-23 | 天津药物研究院 | Method for detecting N-(N-benzoyl- phenylalanyl)-phenylalanine dipeptide derivative |
| CN104289210A (en) * | 2014-07-02 | 2015-01-21 | 苏州苏凯路化学科技有限公司 | Preparation method of novel phenylalanine chiral chromatographic column stationary phase |
| CN105021681A (en) * | 2015-07-08 | 2015-11-04 | 常州大学 | Chitosan-modified glassy carbon electrode-based selective recognition of tryptophan enantiomer containing zinc ion |
| CN105758915A (en) * | 2016-03-02 | 2016-07-13 | 常州大学 | Preparation of carboxymethyl cellulose-chitosan composite material and identification of tryptophan enantiomer by modified electrode of composite material through electrochemical process |
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2017
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| CN102466659A (en) * | 2010-11-15 | 2012-05-23 | 天津药物研究院 | Method for detecting N-(N-benzoyl- phenylalanyl)-phenylalanine dipeptide derivative |
| CN104289210A (en) * | 2014-07-02 | 2015-01-21 | 苏州苏凯路化学科技有限公司 | Preparation method of novel phenylalanine chiral chromatographic column stationary phase |
| CN105021681A (en) * | 2015-07-08 | 2015-11-04 | 常州大学 | Chitosan-modified glassy carbon electrode-based selective recognition of tryptophan enantiomer containing zinc ion |
| CN105758915A (en) * | 2016-03-02 | 2016-07-13 | 常州大学 | Preparation of carboxymethyl cellulose-chitosan composite material and identification of tryptophan enantiomer by modified electrode of composite material through electrochemical process |
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| 溶剂挥发诱导苯丙氨酸二肽自组装结构的电化学生物传感研究;刘丹等;《应用化工》;20130531;第42卷(第5期);全文 |
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