CN106153589B - Cup pyridine is in neutral physiological ph aqueous solution to the Selective recognition method of acidic amino acid - Google Patents
Cup pyridine is in neutral physiological ph aqueous solution to the Selective recognition method of acidic amino acid Download PDFInfo
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Abstract
The invention discloses a kind of glass of pyridines in neutral physiological ph aqueous solution to the method for acidic amino acid Selective recognition, its step is to be uniformly mixed to obtain solution after cup pyridine and pyrene tetrasulfonic acid tetrasodium salt are dissolved in the water, and then carries out fluorometric investigation at room temperature to the solution；Then 20 kinds of natural amino acids are added separately in above-mentioned solution, fluorometric investigation is carried out at room temperature respectively again to acquired solution after one minute；It finally will lead to the changed amino acid of fluorescence signal and its be dissolved in deuterium-oxide with the mixture of cup pyridine, nuclear magnetic resonance spectroscopy test is carried out respectively at room temperature to acquired solution.The present invention realizes the application to the bioactive substance acidic amino acid peptide being condensed into and the detection of acidic amino acid metabolite fluorescence sense using Selective recognition of the cup pyridine to acidic amino acid.Thus, cup pyridine has extensive potential using value in biomedicine field to the Selective recognition of acidic amino acid in neutral physiological ph aqueous solution.
Description
This patent obtain state natural sciences fund youth Projects (21402141), Tianjin application foundation with
Cutting edge technology research plan (young project) (15JCQNJC05400), technician introduction fund project (natural section of Tianjin Normal University
Learn) the open research foundation project subsidy of (5RL122) and city-level key lab of Tianjin Normal University.
Technical field
The invention belongs to Supramolecular Recognition method and technology fields, are related to glass pyridine in neutral physiological ph aqueous solution to acid
The method of the Selective recognition of acidic amino acid.
Background technique
Amino acid is the basic structure substance for constituting protein macromolecule, not only participates in enzyme, hormone, peptide and other in human body
The synthesis process of critical function albumen, and it is all closely bound up with human body items physiological activity and metabolism, it is in organism
The indispensable important component of the synthesis of protein, referring to: 1) A. Isidro-Llobet, M. Alvarez, F.
Albericio. Chem. Rev.2009, 109, 2455−2504;2) F. J. Sardina, H. Rapoport.Chem. Rev. 1996, 96, 1825−1872.The amino acid that may participate in protein synthesis in human body has 20 kinds, according to its side
The structure and physicochemical property of chain can fall into 5 types, non-polar aliphatic amino acid, polar neutral amino acid, the amino containing aromatic rings
Acid, basic amino acid and acidic amino acid, wherein non-polar aliphatic amino acid, polar neutral amino acid and the ammonia containing aromatic rings
Base acid is all neutral amino acid.There is important theoretical meaning in biomedicine field to the Selective recognition of particular types amino acid
Adopted and potential application value, thus the research of the Selective recognition and detection to particular types amino acid is constantly subjected to scientist
Very big concern, referring to 1) A. Acharya, B. Ramanujam, J. P. Chinta, C. P. Rao.J. Org. Chem2011,76, 127−137;2) X.-Q. Chen, Y. Zhou, X.-J. Peng, J.-Y. Yoon. Chem. Soc. Rev. 2010, 39, 2120−2135;3) N. Hayashi, S. Jin, T. Ujihara.Tetrahedron Lett. 2015, 56, 5557−5560.It is mostly selectivity of the big ring of anion to basic amino acid in current existing report
Identification, referring to: 1) C. Li, J. Ma, L. Zhao, Y. Zhang, Y. Yu, X. Shu, J. Li, X. Jia,Chem. Commun.2013, 49, 1924−1926;2) N. Douteau-Gu é vel, A. W. Coleman, J.-P.
Morel,N. Morel-Desrosiers, J. Chem. Soc., Perkin Trans. 21999,629−633.However it is right
The research of acidic amino acid Selective recognition is also rarely reported.
Cup pyridine is a kind of cyclic compound for being rich in pyridylium, have it is good water-soluble and with anion visitor
The potential of body bonding.The compound synthesize using 3- bromo methyl cycloheptapyridine as raw material simple and effective, referring to: S.
Shinoda, M. Tadokoro, H. Tsukube, R. Arakawa, Chem. Commun.1998, 181−182.So
And it is also rarely reported based on the application of the supermolecule of cup pyridine.
Summary of the invention
The purpose of the present invention is analyzing in view of the above technology, it is right in neutral physiological ph aqueous solution to provide a kind of glass of pyridine
The method of acidic amino acid Selective recognition, and using the method achieve the peptide Glu-Glu being condensed into acidic amino acid and
Detection to acidic amino acid metabolite α-ketoglutaric acid.
To achieve the above object, the invention discloses following technology contents:
To the method for acidic amino acid Selective recognition in neutral physiological ph aqueous solution, feature exists a kind of glass of pyridine
It is carried out in by following step:
1) it is uniformly mixed after cup pyridine, pyrene tetrasulfonic acid tetrasodium salt being dissolved in the water and obtains solution, the cup pyridine and pyrene
Tetrasulfonic acid tetrasodium salt concentration is respectively 0.004 mmol/L and 0.001 mmol/L, then carries out fluorescence at room temperature to the solution
Test；
2) 20 kinds of natural amino acids are added separately in above-mentioned solution, amino acid concentration is 1 mmol/L, the amino
Acid includes neutral amino acids alanine, valine, leucine, isoleucine, methionine, phenylalanine, serine, Soviet Union's ammonia
Acid, asparagine, glutamine, tyrosine, tryptophan, cysteine, proline, glycine, basic amino acid histidine,
Arginine, lysine and acidic amino acid glutamic acid, asparatate.Acquired solution is distinguished again after being added amino acid one minute
Fluorometric investigation is carried out at room temperature；
3) will be added after amino acid in step (2) causes a glass pyridine-pyrene tetrasulfonic acid tetrasodium salt aqueous solution fluorescence signal to be sent out
The mixture of the amino acid for changing and these amino acid and cup pyridine, which is dissolved separately in be uniformly mixed in deuterium-oxide, obtains difference
Solution, then to these deuterium-oxide solution at room temperature respectively carry out nuclear magnetic resonance spectroscopy test；The amino acid and cup pyridine
Concentration be 5 mmol/L.
The present invention further discloses cup pyridine to acidic amino acid Selective recognition in neutral physiological ph aqueous solution
Method is in the peptide Glu-Glu being condensed into acidic amino acid and to acidic amino acid metabolite α-ketoglutaric acid context of detection
Using.Wherein the detection of the peptide Glu-Glu being condensed into acidic amino acid refers to: when Glu-Glu is added to a glass pyrrole
When in pyridine-pyrene tetrasulfonic acid tetrasodium salt aqueous solution, apparent variation occurs for the fluorescence signal of pyrene tetrasulfonic acid tetrasodium salt, by hypofluorescence
Transmitting signal is changed into hyperfluorescence transmitting signal.It is described that the detection of acidic amino acid metabolite α-ketoglutaric acid is referred to
Be: when α-ketoglutaric acid is added in a glass pyridine-pyrene tetrasulfonic acid tetrasodium salt aqueous solution, the fluorescence of pyrene tetrasulfonic acid tetrasodium salt is believed
Number apparent variation occurs, hyperfluorescence transmitting signal is changed by hypofluorescence transmitting signal.
More detailed description of the present invention is as follows:
Cup pyridine is bonded with acidic amino acid to the property of can choose, as macrocyclic host to neutral amino acid and alkaline ammonia
Base acid does not have bonding action；Wherein the structure of cup pyridine and acidic amino acid is as follows:
When the histidine in neutral amino acid or basic amino acid is added to a glass pyridine-pyrene tetrasulfonic acid tetrasodium salt aqueous solution
When middle, the fluorescence signal of pyrene tetrasulfonic acid tetrasodium salt does not change, still be hypofluorescence emit signal, show above-mentioned amino acid and
Cup pyridine is without bonding.
When lysine, arginine or the acidic amino acid in basic amino acid are added to a glass pyridine-pyrene tetrasulfonic acid tetrasodium salt
When in aqueous solution, apparent variation occurs for the fluorescence signal of pyrene tetrasulfonic acid tetrasodium salt, is changed by hypofluorescence transmitting signal strong glimmering
Light emission signal；Hydrogen nuclear magnetic resonance stave is carried out respectively to above-mentioned amino acid and above-mentioned amino acid-cup pyridine deuterium-oxide solution
Sign, as the result is shown lysine and arginine in the presence of cup pyridine on amino acid the chemical shift of all hydrogen atoms and its
Compared to variation is not subjected to displacement when individualism, show that the lysine in basic amino acid, arginine are added to a glass pyridine-
Cause when in pyrene tetrasulfonic acid tetrasodium salt aqueous solution pyrene tetrasulfonic acid tetrasodium salt generate fluorescence signal variation not be glass pyridine and
Caused by lysine, arginine bonding, lysine, arginine and cup pyridine are without bonding；And acidic amino acid exists in cup pyridine
In the case where on amino acid all hydrogen atoms chemical shift with its individualism when compared apparent change in displacement, show acid
Acidic amino acid causes pyrene tetrasulfonic acid tetrasodium salt to generate fluorescence letter when being added in a glass pyridine-pyrene tetrasulfonic acid tetrasodium salt aqueous solution
Number variation be caused by glass pyridine and acidic amino acid are bonded, acidic amino acid and cup pyridine have bonding.
The detection for the peptide Glu-Glu that acidic amino acid is condensed into is referred to: when Glu-Glu is added to a glass pyridine-pyrene four
When in sulfonic acid tetrasodium salt aqueous solution, apparent variation occurs for the fluorescence signal of pyrene tetrasulfonic acid tetrasodium salt, emits signal by hypofluorescence
It is changed into hyperfluorescence transmitting signal.The detection of acidic amino acid metabolite α-ketoglutaric acid is referred to: working as α-ketoglutaric acid
When being added in a glass pyridine-pyrene tetrasulfonic acid tetrasodium salt aqueous solution, apparent become occurs for the fluorescence signal of pyrene tetrasulfonic acid tetrasodium salt
Change, hyperfluorescence transmitting signal is changed by hypofluorescence transmitting signal.
Cup pyridine disclosed by the invention is in neutral physiological ph aqueous solution to the method for acidic amino acid Selective recognition
It is possessed to have the active effect that
Cup pyridine is neutral physiological ph aqueous solution to the medium of acidic amino acid Selective recognition；Cup pyridine is to acid ammonia
The characterizing method high-efficient simple of base acid Selective recognition；It is realized using Selective recognition of the cup pyridine to acidic amino acid to life
The application for peptide and acidic amino acid metabolite the fluorescence sense detection that active substances acidic amino acid is condensed into.Thus, cup
Pyridine has extensive dive in biomedicine field to the Selective recognition of acidic amino acid in neutral physiological ph aqueous solution
In application value.
[Detailed description of the invention]
Fig. 1 is cup pyridine-pyrene tetrasulfonic acid tetrasodium salt, cup pyridine-pyrene tetrasulfonic acid tetrasodium salt-amino acid solution is glimmering
Light spectrogram, wherein cup pyridine concentration is 0.004 mmol/L, and pyrene tetrasulfonic acid tetrasodium salt concentration is 0.001 mmol/L, amino acid
Concentration is 1 mmol/L, and amino acid includes glutamic acid, asparatate, histidine, arginine, lysine, alanine, figured silk fabrics ammonia
Acid, leucine, isoleucine, methionine, phenylalanine, serine, threonine, asparagine, glutamine, junket ammonia
Acid, tryptophan, cysteine, proline, glycine；
Fig. 2 is the core of glutamic acid (label is in attached drawing) and cup pyridine-glutamic acid (label is in attached drawing) deuterium-oxide solution
Magnetic resonance hydrogen spectrogram, Glutamic Acid and cup pyridine concentration are all 5 mmol/L；
Fig. 3 is asparatate (label is in attached drawing) and cup pyridine-asparatate (label is in attached drawing) deuterium-oxide
The hydrogen nuclear magnetic resonance spectrogram of solution, wherein asparatate and cup pyridine concentration are all 5 mmol/L；
Fig. 4 is the core of arginine (label is in attached drawing) and cup pyridine-arginine (label is in attached drawing) deuterium-oxide solution
Magnetic resonance hydrogen spectrogram, wherein arginine and cup pyridine concentration are all 5 mmol/L；
Fig. 5 is the core of lysine (label is in attached drawing) and cup pyridine-lysine (label is in attached drawing) deuterium-oxide solution
Magnetic resonance hydrogen spectrogram, wherein lysine and cup pyridine concentration are all 5 mmol/L；
Fig. 6 is in the presence of cup pyridine, and glutamic acid (Glu is abbreviated as in attached drawing), asparatate (contract in attached drawing
Be written as Asp), on arginine (being abbreviated as Arg in attached drawing) and lysine (being abbreviated as Lys in attached drawing) each Hydrogen Proton chemical potential
Move changing value figure；
Fig. 7 is the addition for the peptide Glu-Glu being condensed into acidic amino acid, and cup pyridine-pyrene tetrasulfonic acid tetrasodium salt is water-soluble
The variation diagram of liquid fluorescent emission intensity, wherein the concentration of cup pyridine is 0.004 mmol/L, and the concentration of pyrene tetrasulfonic acid tetrasodium salt is
0.001 mmol/L；
Fig. 8 is the addition with acidic amino acid metabolite α-ketoglutaric acid, cup pyridine-pyrene tetrasulfonic acid tetrasodium salt water
The variation diagram of solution fluorescence emissive porwer, wherein the concentration of cup pyridine is 0.004 mmol/L, the concentration of pyrene tetrasulfonic acid tetrasodium salt
For 0.001 mmol/L.
Specific embodiment
Illustrate the present invention below with reference to embodiment, the scheme of embodiment described here does not limit the present invention, this field it is special
Industry personnel spirit according to the invention can make improvements and change, and the such modifications and variations are regarded as at this
In the range of invention, the scope of the present invention and essence are defined by the claims.Wherein pyrene tetrasulfonic acid tetrasodium salt, 20 kinds of amino
Acid, Glu-Glu and α-ketoglutaric acid are commercially available.Cup pyridine is synthesize using 3- bromo methyl cycloheptapyridine as raw material simple and effective
, referring to: S. Shinoda, M. Tadokoro, H. Tsukube, R. Arakawa,Chem. Commun. 1998,
181−182。
Embodiment 1
To the method for acidic amino acid Selective recognition in neutral physiological ph aqueous solution, feature exists a kind of glass of pyridine
It is carried out in by following step:
1) it is uniformly mixed after cup pyridine, pyrene tetrasulfonic acid tetrasodium salt being dissolved in the water and obtains solution, the cup pyridine and pyrene
Tetrasulfonic acid tetrasodium salt concentration is respectively 0.004 mmol/L and 0.001 mmol/L, then carries out fluorescence at room temperature to the solution
Test；
2) 20 kinds of natural amino acids are added separately in above-mentioned solution, amino acid concentration is 1 mmol/L, the amino
Acid includes neutral amino acids alanine, valine, leucine, isoleucine, methionine, phenylalanine, serine, Soviet Union's ammonia
Acid, asparagine, glutamine, tyrosine, tryptophan, cysteine, proline, glycine, basic amino acid histidine,
Arginine, lysine and acidic amino acid glutamic acid, asparatate.Acquired solution is distinguished again after being added amino acid one minute
Fluorometric investigation is carried out at room temperature；
3) a glass pyridine-pyrene tetrasulfonic acid tetrasodium salt aqueous solution fluorescence signal will be caused to become after above-mentioned addition amino acid
The mixture of the amino acid of change and these amino acid and cup pyridine, which is dissolved in be uniformly mixed in deuterium-oxide, obtains solution, the amino
The concentration of acid and cup pyridine is 5 mmol/L, then carries out nuclear magnetic resonance spectroscopy survey respectively at room temperature to these deuterium-oxide solution
Examination.
Embodiment 2:
A kind of glass of pyridine is in neutral physiological ph aqueous solution to the method for acidic amino acid Selective recognition:
1) cup pyridine passes through fluorescence spectrum hand to the Selective recognition of acidic amino acid in neutral physiological ph aqueous solution
Segment table sign, Fig. 1 are cup pyridine-pyrene tetrasulfonic acid tetrasodium salt, cup pyridine-pyrene tetrasulfonic acid tetrasodium salt-amino acid solution fluorescence
Launching light spectrogram, wherein cup pyridine concentration is 0.004 mmol/L, and pyrene tetrasulfonic acid tetrasodium salt concentration is 0.001 mmol/L, amino
Acid concentration is 1 mmol/L, and amino acid includes acidic amino acid glutamic acid, asparatate, basic amino acid histidine, smart ammonia
Acid, lysine and neutral amino acids alanine, valine, leucine, isoleucine, methionine, phenylalanine, serine,
Threonine, asparagine, glutamine, tyrosine, tryptophan, cysteine, proline, glycine；It is shown in figure, in the middle
When histidine in acidic amino acid or basic amino acid is added in a glass pyridine-pyrene tetrasulfonic acid tetrasodium salt aqueous solution, pyrene tetrasulfonic acid
The fluorescence signal of tetrasodium salt does not change, and still emits signal for hypofluorescence, shows above-mentioned amino acid and cup pyridine without bonding；
When lysine, arginine or the acidic amino acid in basic amino acid are added in a glass pyridine-pyrene tetrasulfonic acid tetrasodium salt aqueous solution
When, apparent variation occurs for the fluorescence signal of pyrene tetrasulfonic acid tetrasodium salt, is changed into hyperfluorescence transmitting letter by hypofluorescence transmitting signal
Number；
2) cup pyridine passes through magnetic resonance spectroscopy table to the Selective recognition of acidic amino acid in neutral physiological ph aqueous solution
Sign, Fig. 2 are that glutamic acid (label is in attached drawing) and cup pyridine-glutamic acid (mark and are) nuclear-magnetism of deuterium-oxide solution total in attached drawing
Shake hydrogen spectrogram；Fig. 3 is asparatate (label is in attached drawing) and cup pyridine-asparatate (label is in attached drawing) deuterium
The hydrogen nuclear magnetic resonance spectrogram of aqueous solution；Fig. 4 is that arginine (label is in attached drawing) and cup pyridine-arginine (mark in attached drawing
For the hydrogen nuclear magnetic resonance spectrogram of b) deuterium-oxide solution；Fig. 5 is lysine (label is in attached drawing) and cup pyridine-lysine (attached drawing
Middle label is) hydrogen nuclear magnetic resonance spectrogram of deuterium-oxide solution, wherein the concentration of amino acid and cup pyridine is all 5 mmol/L；Fig. 6 is
In the presence of cup pyridine, glutamic acid (Glu is abbreviated as in attached drawing), asparatate (Asp is abbreviated as in attached drawing), smart ammonia
The chemical shift changing value figure of each Hydrogen Proton on sour (being abbreviated as Arg in attached drawing) and lysine (being abbreviated as Lys in attached drawing), figure
The chemical shift of all hydrogen atoms is independent with it on amino acid in the presence of cup pyridine for middle display, lysine and arginine
In the presence of compared to not being subjected to displacement variation, show that the lysine in basic amino acid, arginine are added to a glass pyridine-pyrene four
The variation for the fluorescence signal for causing pyrene tetrasulfonic acid tetrasodium salt to generate when in sulfonic acid tetrasodium salt aqueous solution is not glass pyridine and bad ammonia
Caused by acid, arginine bonding, lysine, arginine and cup pyridine are without bonding；And acidic amino acid feelings existing for cup pyridine
Under condition on amino acid the chemical shift of all hydrogen atoms with its individualism when compared apparent change in displacement, show acid ammonia
Base acid causes pyrene tetrasulfonic acid tetrasodium salt to generate fluorescence signal when being added in a glass pyridine-pyrene tetrasulfonic acid tetrasodium salt aqueous solution
Caused by variation is glass pyridine and acidic amino acid bonding, acidic amino acid and cup pyridine have bonding.
Embodiment 3
2 glasss of pyridines of embodiment are in neutral physiological ph aqueous solution to the method for acidic amino acid Selective recognition to acidity
Amino acid condensation at peptide Glu-Glu detection application, the method is as follows:
It is uniformly mixed after cup pyridine, pyrene tetrasulfonic acid tetrasodium salt are dissolved in the water and obtains solution, the cup pyridine and pyrene four
Sulfonic acid tetrasodium salt concentration is respectively 0.004 mmol/L and 0.001 mmol/L.As shown in fig. 7, as acidic amino acid is condensed into
Peptide Glu-Glu be added gradually in above-mentioned cup pyridine-pyrene tetrasulfonic acid tetrasodium salt aqueous solution, the fluorescence of pyrene tetrasulfonic acid tetrasodium salt
Signal is gradually converted into hyperfluorescence transmitting signal by hypofluorescence transmitting signal, to realize the peptide being condensed into acidic amino acid
The application of the fluorescence sense detection of Glu-Glu.
Embodiment 4
2 glasss of pyridines of embodiment are in neutral physiological ph aqueous solution to the method for acidic amino acid Selective recognition to acidity
The application of the detection of amino acid metabolites α-ketoglutaric acid, the method is as follows:
It is uniformly mixed after cup pyridine, pyrene tetrasulfonic acid tetrasodium salt are dissolved in the water and obtains solution, the cup pyridine and pyrene four
Sulfonic acid tetrasodium salt concentration is respectively 0.004 mmol/L and 0.001 mmol/L.As shown in figure 8, being produced as acidic amino acid is metabolized
Object α-ketoglutaric acid is added gradually in above-mentioned cup pyridine-pyrene tetrasulfonic acid tetrasodium salt aqueous solution, the fluorescence of pyrene tetrasulfonic acid tetrasodium salt
Signal is gradually converted into hyperfluorescence transmitting signal by hypofluorescence transmitting signal, to realize to acidic amino acid metabolite α-
The application of the fluorescence sense detection of ketoglutaric acid.
Claims (2)
1. a kind of glass of pyridine is in neutral physiological ph aqueous solution to the method for acidic amino acid Selective recognition, it is characterised in that
It is carried out by following step:
1) cup pyridine and pyrene tetrasulfonic acid tetrasodium salt are dissolved in the water uniformly mixed, obtain a glass pyridine-pyrene tetrasulfonic acid tetrasodium salt water
Solution, cup pyridine and pyrene tetrasulfonic acid tetrasodium salt concentration are respectively 0.004 mmol/L and 0.001 mmol/L, then to the solution
Fluorometric investigation is carried out at room temperature；
2) 20 kinds of natural amino acids are added separately in above-mentioned solution, amino acid concentration is 1 mmol/L, and amino acid one is added
Fluorometric investigation is carried out at room temperature respectively again to acquired solution after minute；The amino acid includes neutral amino acids alanine, figured silk fabrics
Propylhomoserin, leucine, isoleucine, methionine, phenylalanine, serine, threonine, asparagine, glutamine, junket ammonia
Acid, tryptophan, cysteine, proline, glycine, basic amino acid histidine, arginine, lysine and acidic amino acid paddy
Propylhomoserin, asparatate；
3) a glass pyridine-pyrene tetrasulfonic acid tetrasodium salt aqueous solution fluorescence signal is caused to become after amino acid being added in step 2)
The mixture of the amino acid of change and these amino acid and cup pyridine be dissolved separately in deuterium-oxide be uniformly mixed obtain it is different molten
Liquid then carries out nuclear magnetic resonance spectroscopy test to these deuterium-oxide solution respectively at room temperature；The amino acid and cup pyridine it is dense
Degree is 5 mmol/L.
2. described in claim 1 glass of pyridine exists to acidic amino acid Selective recognition method in neutral physiological ph aqueous solution
The peptide Glu-Glu be condensed into acidic amino acid and the application to acidic amino acid metabolite α-ketoglutaric acid context of detection,
Wherein the detection of the peptide Glu-Glu being condensed into acidic amino acid refers to: when Glu-Glu is added to a glass pyridine-pyrene
When in tetrasulfonic acid tetrasodium salt aqueous solution, apparent variation occurs for the fluorescence signal of pyrene tetrasulfonic acid tetrasodium salt, is emitted by hypofluorescence and is believed
Number it is changed into hyperfluorescence transmitting signal, the detection to acidic amino acid metabolite α-ketoglutaric acid refers to: as α-
When ketoglutaric acid is added in a glass pyridine-pyrene tetrasulfonic acid tetrasodium salt aqueous solution, the fluorescence signal of pyrene tetrasulfonic acid tetrasodium salt occurs bright
Aobvious variation is changed into hyperfluorescence transmitting signal by hypofluorescence transmitting signal.
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| WO2003018548A2 (en) * | 2001-08-24 | 2003-03-06 | Board Of Regents, The University Of Texas System | Halogenated calixpyrroles, calixpyridinopyrroles and calixpyridines, and uses thereof |
| CN105130882A (en) * | 2015-07-15 | 2015-12-09 | 天津师范大学 | Construction of sulfonated calyx[4]arene-methyl-naphthyl-viologen simulative biologic region selective recognition bionic system |
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| WO2003018548A2 (en) * | 2001-08-24 | 2003-03-06 | Board Of Regents, The University Of Texas System | Halogenated calixpyrroles, calixpyridinopyrroles and calixpyridines, and uses thereof |
| CN105130882A (en) * | 2015-07-15 | 2015-12-09 | 天津师范大学 | Construction of sulfonated calyx[4]arene-methyl-naphthyl-viologen simulative biologic region selective recognition bionic system |
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| Title |
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| A calixpyridinium-based supramolecular tandem assay for alkaline phosphatase and its application to ATP hydrolysis reaction;Kui Wang et al.;《Organic & Biomolecular Chemistry》;20160126;第14卷(第9期);2685-2689 * |
| One-step synthesis of a quaternary tetrapyridinium macrocycle as a new specific receptor of tricarboxylate anions;Satoshi Shinoda et al.;《Chem. Commun.》;19980101(第2期);181-182 * |
| Shao-Yong Li et al..Highly selective fluorescent calix[4]arene chemosensor for acidic amino acids in pure aqueous media.《Tetrahedron Letters》.2012,第53卷(第23期),2919-2920. * |
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