CN105753727A - Method for selectively separating amino acid optical isomers through molecular imprinting polypyrrole electrode mast - Google Patents
Method for selectively separating amino acid optical isomers through molecular imprinting polypyrrole electrode mast Download PDFInfo
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- CN105753727A CN105753727A CN201610102813.0A CN201610102813A CN105753727A CN 105753727 A CN105753727 A CN 105753727A CN 201610102813 A CN201610102813 A CN 201610102813A CN 105753727 A CN105753727 A CN 105753727A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
- C07C227/34—Preparation of optical isomers by separation of optical isomers
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- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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Abstract
The invention relates to a method for selectively separating amino acid optical isomers through a molecular imprinting polypyrrole electrode mast. The method comprises the steps of preparing a molecular imprinting polypyrrole powder with L amino acid as a template molecule, preparing the molecular imprinting polypyrrole electrode mast, undoping the L amino acid, gathering amino acid and detecting the amino acid. The method has the advantages that a molecular imprinting polypyrrole material with the L amino acid as a template is synthesized through a chemical oxidizing method and serves as a conductive stationary phase, the molecular imprinting polypyrrole material is filled and prepared into an electrode type chromatographic column, a good characteristic that conductive high polymer is reversible in doping and undoping is utilized, a molecular imprinting technical principle is combined, a separating device of an imitation-ion chromatography is utilized, the amino acid optical isomers can be separated by adjusting and controlling electric potential, and the electrode mast technique can avoid an expensive chiral derivatization agent or chiral fixed phase required by a chromatography method which is used for separating amino acid enantiomers. Furthermore, the method is low in cost, high in efficiency and free of pollution.
Description
Technical field
The invention belongs to electrochemical analysis and separation field, relate to a kind of by the choosing of molecular engram Platinum post
The method of selecting property amino acid separation optical isomer.
Background technology
Amino acid is the basic structural unit of protein, is also a kind of typical life active compound.Great majority
Amino acid all has chiral isomer, and D type and L-type amino acid usually have distinct medical value
And nutrition significance.In recent years, existing Many researchers is devoted to the fractionation amino acid sought easily and fast
The method of optical isomer.They specifically include that chemical method, enzymatic method, chromatography, capillary electrophoresis
With extraction etc..The separation method splitting amino acid enantiomer conventional has a lot, but so far, the most not
Can find one inexpensive efficiently, applicable surface more extensively and again can the method for heavy industrialization.
Originating from the molecular imprinting of the thirties in 20th century, the solution for this difficult problem provides good
Opportunity.It originates from a kind of using antigen as template, utilizes specific reaction " casting " at the sky of antibody
Between the theory of binding site.The theory of this novelty is through the development of decades, until the seventies and eighties,
It is applied to practice.1973, Wulff etc. was prepared for can be used in the molecular engram polymerization of chiral resolution first
Thing (MIPs), lays a good foundation for molecularly imprinted polymer application in terms of separation.
All there is chiral enantiomer (except glycine) based on amino acid, and between amino acid molecular structurally
There is certain similitude, therefore using conducting polymer as molecular engram material, be applied to chiral isomer
Chromatographic isolation has vast potential for future development, also moves towards scale and a kind of new for biological molecular imprinting
The development of Chiral Separation technology is laid a good foundation.At present, the chiral ammonia of domestic and international application molecular imprinting
The research that base acid and derivative thereof carry out separating needs to derive mostly, and its preparation process is loaded down with trivial details, and reaction system is special
Very so that its application is very limited.
Existing a part of researcher as the matrix of chromatograph packing material, passes through electrochemistry with conductive material replacement silica gel
Method realizes the Reasonable Regulation And Control of phase fixing to conduction, improves the separative efficiency to sample.But due to amino acid
Enantiomer molecule all shows identical charge property under same acidity condition, so to realize theirs
Separate molecular imprinting to be introduced.
Therefore, research and development one is used by conducting polymer and utilizes molecular imprinting to imitate chromatographic isolation hand
The preparation method of acidic amino acid, is of great significance tool.Compared with existing research work, poly-pyrrole
Cough up the excellent characteristic as a kind of conducting polymer composite with redox reversible.
Summary of the invention
The technical problem to be solved in the present invention is: based on the problems referred to above, and the present invention provides a kind of by molecular engram
The method of Platinum post Selective Separation amino acid optical isomer.
The present invention solves the technical scheme that its technical problem used: a kind of by molecular engram polypyrrole
The method of electrode column Selective Separation amino acid optical isomer, comprises the following steps:
(1) l-amino acid is the preparation of molecular engram polypyrrole powder of template molecule: add L-in aqueous phase
Amino acid, pyrroles and oxidant ,-2～2 DEG C are reacted 8～12 hours, and system pH controls 6.5～8.0；
Suction filtration obtains filter cake, is dried, obtains molecular engram polypyrrole powder；
(2) preparation of molecular engram Platinum post: by powder filled for molecular engram polypyrrole to earthenware
In；
(3) l-amino acid go doping: using preparation molecular engram Platinum post as working electrode,
Saturated calomel electrode is as reference electrode, and platinum electrode is that auxiliary electrode forms three-electrode system, sloughs template and divides
Sub-l-amino acid；
(4) amino acid whose enrichment: slough the molecular engram Platinum on-column enrichment L-amino of template molecule
Acid and D-amino acid；
(5) amino acid whose detection: secondary goes doping, by fluorescence spectrum figure and differential pulse voltammetry figure to two
Secondary go doped solution to be analyzed, calculate enrichment l-amino acid over the electrode shaft and the amino acid whose content of D-,
Obtain l-amino acid and the amino acid whose separation factor of D-.
Further, amino acid is the amino acid containing aromatic hydrocarbons or the amino acid Han heterocyclic, including tryptophan,
Phenylalanine, tyrosine, proline and histidine, template molecule amino acid and enrichment, the amino acid of detection
Kind is consistent.
Further, in step (1), the mol ratio of l-amino acid and pyrroles is 1:1000～1:1100,
Oxidant is FeCl3、(NH4)2S2O8、Fe(ClO4)3Or H2O2, the mol ratio of oxidant and pyrroles be 1:1～
1:2.2.
Further, the preparation of step (2) Middle molecule trace Platinum post method particularly includes: will lead
Voltolisation pyrroles is powder filled to the earthenware of one end closing, is fully compacted, is simultaneously embedded in a stainless steel wire
As wire to realize the conducting between electrochemical workstation and electrode, then with rubber stopper, the other end is sealed.
For making flowing flow through powder in earthenware the most smoothly, on the rubber stopper at two ends, each drill diameter is about the hole of 3mm
(can not be the biggest, it is ensured that water-tight), inserts peristaltic pump tube.A thin layer absorbent cotton is inserted between rubber stopper and powder,
To prevent when flow rate of mobile phase is too big or in post, the fixing phase powder filled is gone out time the highest by pressure, cause compacted
Dynamic pump line is internal blocked.
Further, sloughing template molecule l-amino acid concrete operations in step (3) is: made by peristaltic pump
Buffered phosphate solution flows in molecular engram Platinum post, with buffered phosphate solution as electrolyte,
Constant potential 0.5～1.5V peroxidating 2000～5000s.
Further, step (4) flows in enrichment process mutually for amino acid whose containing l-amino acid and D-
KCl-HCl solution, electrolyte is KCl-HCl solution, constant potential-1.5～-0.1V reductase 12 000～5000s.
The invention has the beneficial effects as follows: use the dividing with l-amino acid as template of chemical oxidization method synthesizing new
Sub-trace electric polypyrrole material, as the fixing phase of conduction, is filled and is prepared as electric pole type chromatographic column (electrode column),
Utilize the good nature of conduction high polymer " doping and dedoping is reversible ", binding molecule engram technology principle,
By the separator of imitative chromatography of ions, with this electrode column as working electrode, form three-electrode system；Pass through
Regulation and control current potential, it is achieved that the separation of amino acid optical isomer；Use electrode column technology can avoid chromatography
Expensive chiral derivatizing agent required during amino acid separation enantiomer or chiral stationary phase, be a kind of inexpensive
Efficiently, and free of contamination separation method.
Detailed description of the invention
Presently in connection with specific embodiment, the invention will be further described, and following example are intended to the present invention is described
Rather than limitation of the invention further.
Embodiment 1
(1) L-Trp (L-Trp) is the preparation of molecular engram polypyrrole powder of template molecule
In beaker, add 35mL contain 0.78mM L-Trp, 0.82M pyrroles and (subtract through secondary before Shi Yonging
Pressure distillation) deionized water, by 20mL 1.14M (NH4)2S2O8It is slowly dropped in reaction system, system
Start micro-in blackish green, then blackening rapidly.Dropping KOH solution regulation system pH value is neutrality, reaction temperature
Degree is maintained at 0 DEG C, continuously stirred 8～10 hours, and reaction terminates rear suction filtration, cleans powder with absolute ethyl alcohol
The oligomer of adsorption and unreacted monomer, rear colourless to filtrate with water cyclic washing.60 DEG C of vacuum are done
Dry 24h is standby.
(2) preparation of molecular engram Platinum post
One end rubber stopper of porous ceramic pipe is tamping, inserts 0.2g electric polypyrrole powder from one end, fill
Dividing potential drop is real, is simultaneously embedded in a stainless steel wire as wire to realize leading between electrochemical workstation and electrode
Logical, then with rubber stopper, the other end is sealed.For making flowing flow through powder in earthenware the most smoothly, at two ends
On rubber stopper, each drill diameter is about the hole of 3mm, inserts peristaltic pump tube.Trace Platinum post by preparation
As working electrode, saturated calomel electrode is as reference electrode, and platinized platinum is that auxiliary electrode forms three-electrode system.
(3) L-Trp go doping
Using the molecular engram Platinum post of preparation as working electrode, platinized platinum is as auxiliary electrode, saturated
Calomel electrode is reference electrode, forms three-electrode system, carries out doping.Remove the process simulation ion look that adulterates
Spectrum separation condition, makes 0.05M PBS (PB) (pH=6.90) flow in electrode column by peristaltic pump
Dynamic, on this basis electrode column is applied+1.0v a current potential, with 0.05M PB solution as electrolyte
(pH=6.90), constant potential peroxidating 5000s, sloughs template molecule (flowing is mutually and medium is total to 50mL).
(4) enrichment of L-Trp and D-Trp
Enrichment process is to carry out in the three-electrode system in step (3).Flowing in enrichment process is 50mL mutually
0.10M KCl-HCl solution (pH=4.0) containing 8.50 μMs of L-Trp and 8.50 μMs of D-Trp, electrolyte is
0.10M KCl-HCl solution (pH=4.00), constant potential-0.4V reduce 4000s.
(5) detection of L-Trp and D-Trp
The electrode column that molecular engram electric polypyrrole with L-Trp as template molecule is filled is after dedoping, rich
Collection 50mL KCl-HCl (pH=4.0) solution containing 8.50 μMs of L-Trp and D-Trp, then in step (3)
Under conditions of again the tryptophan of enrichment is carried out secondary go doping.
With glass-carbon electrode as working electrode, platinized platinum is to electrode, to being enriched L-Trp's and D-Trp respectively
Secondary goes doping liquid to carry out differential pulse voltammetry scanning.Being the peak of tryptophan at 0.62V, its peak current size is deposited
It is being clearly distinguished from, respectively 0.58 μ A and 0.17 μ A.Again by fluorescence method, measure the glimmering of dedoping liquid respectively
Luminous intensity, combined standard working curve, measure the exact level of L-Trp and D-Trp in two parts of solution, and
Calculate its separation factor, the results are shown in Table 1.
Embodiment 2
Tryptophan (Trp) replaces with tyrosine (Tyr), and step (1)～(4) are with embodiment 1.
(5) detection of L-Tyr and D-Tyr
The electrode column that molecular engram electric polypyrrole with L-Tyr as template molecule is filled is after going doping, rich
Collection 50mL 0.10M KCl-HCl (pH=4.0) solution containing 9.80 μMs of L-Tyr and 9.80 μMs of D-Tyr, and
After under conditions of step (3), the tyrosine of enrichment is carried out secondary go doping.
With glass-carbon electrode as working electrode, platinized platinum is to electrode, to being enriched L-Tyr's and D-Tyr respectively
Secondary dedoping liquid carries out differential pulse voltammetry scanning.Tyrosine has two peaks in this sweep limits, respectively
At 0.06V and 0.65V, at two all there is significant difference in peak current size.At 0.65V, L-Tyr and D-Tyr
Peak current be respectively 3.11 μ A and 0.37 μ A；At 0.06V, the peak current of L-Tyr and D-Tyr is respectively
It is 0.48 μ A and 0.21 μ A.Again by fluorescence method, measure secondary respectively and go the fluorescence intensity of doping liquid, in conjunction with
The standard working curve of tyrosine, measures the exact level of L-Tyr and D-Tyr in two parts of solution, and calculates
Its separation factor, the results are shown in Table 1.
The amino acid whose separation factor of L/D-that table 1 identical separation method obtains
Molecular engram electrode column carries out amino acid enantiomer separation by potential inducing method, and separating effect is notable,
Apparently higher than part chromatography, it is shown in Table 2.
The different separation method tryptophan of table 2 and the comparison of the tyrosine Chiral Separation factor
With the above-mentioned desirable embodiment according to the present invention for enlightenment, by above-mentioned description, related work
Personnel can be carried out various change and repair completely in the range of without departing from this invention technological thought
Change.The content that the technical scope of this invention is not limited on specification, it is necessary to according to claim
Scope determines its technical scope.
Claims (6)
1. by a method for molecular engram Platinum post Selective Separation amino acid optical isomer, its
Feature is: comprise the following steps:
(1) l-amino acid is the preparation of molecular engram polypyrrole powder of template molecule: add L-in aqueous phase
Amino acid, pyrroles and oxidant ,-2～2 DEG C are reacted 8～12 hours, and system pH controls 6.5～8.0；
Suction filtration obtains filter cake, is dried, obtains molecular engram polypyrrole powder；
(2) preparation of molecular engram Platinum post: by powder filled for molecular engram polypyrrole to earthenware
In；
(3) l-amino acid go doping: using preparation molecular engram Platinum post as working electrode,
Saturated calomel electrode is as reference electrode, and platinum electrode is that auxiliary electrode forms three-electrode system, sloughs template and divides
Sub-l-amino acid；
(4) amino acid whose enrichment: slough the molecular engram Platinum on-column enrichment L-amino of template molecule
Acid and D-amino acid；
(5) amino acid whose detection: secondary goes doping, by fluorescence spectrum figure and differential pulse voltammetry figure to two
Secondary go doped solution to be analyzed, calculate enrichment l-amino acid over the electrode shaft and the amino acid whose content of D-,
Obtain l-amino acid and the amino acid whose separation factor of D-.
One the most according to claim 1 is by molecular engram Platinum post Selective Separation amino acid
The method of optical isomer, is characterized in that: described amino acid is the amino acid containing aromatic hydrocarbons or contains heterocyclic
Amino acid, including tryptophan, phenylalanine, tyrosine, proline and histidine, template molecule amino acid
Consistent with the amino acid classes of enrichment, detection.
One the most according to claim 1 is by molecular engram Platinum post Selective Separation amino acid
The method of optical isomer, is characterized in that: in described step (1), the mol ratio of l-amino acid and pyrroles is
1:1000～1:1100, oxidant is FeCl3、(NH4)2S2O8、Fe(ClO4)3Or H2O2, oxidant and pyrrole
The mol ratio coughed up is 1:1～1:2.2.
One the most according to claim 1 is by molecular engram Platinum post Selective Separation amino acid
The method of optical isomer, is characterized in that: the system of described step (2) Middle molecule trace Platinum post
Standby method particularly includes: fully it is compacted powder filled for electric polypyrrole to the earthenware of one end closing,
It is simultaneously embedded in a stainless steel wire as wire, then with rubber stopper, the other end is sealed, at the rubber stopper at two ends
Upper each drill diameter is about the hole of 3mm, inserts peristaltic pump tube, inserts a thin layer absorbent cotton between rubber stopper and powder.
One the most according to claim 1 is by molecular engram Platinum post Selective Separation amino acid
The method of optical isomer, is characterized in that: slough template molecule l-amino acid in described step (3) concrete
Operation is: make buffered phosphate solution flow in molecular engram Platinum post by peristaltic pump, with slow
Rushing phosphate solution is electrolyte, constant potential 0.5～1.5V peroxidating 2000～5000s.
One the most according to claim 1 is by molecular engram Platinum post Selective Separation amino acid
The method of optical isomer, is characterized in that: flow in enrichment process in described step (4) mutually for containing L-
Amino acid and D-amino acid whose KCl-HCl solution, electrolyte is KCl-HCl solution, constant potential-1.5～-0.1
V reductase 12 000～5000s.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106928434A (en) * | 2017-03-07 | 2017-07-07 | 常州大学 | A kind of method and its application by the tartrate ion synthesis of chiral conducting polymer that adulterates |
| CN107121470A (en) * | 2017-05-08 | 2017-09-01 | 常州大学 | The preparation of molecular engram overoxidised polypyrrole/manganese dioxide/carbon felt composite material |
| CN107219277A (en) * | 2017-05-08 | 2017-09-29 | 常州大学 | The preparation of molecular engram overoxidised polypyrrole/poly- p-aminobenzene sulfonic acid modified electrode |
| CN110243902A (en) * | 2019-02-25 | 2019-09-17 | 常州大学 | A kind of bimolecular trace silica/Pt/Polypyrrole composite material preparation method that can identify alanine and tyrosine enantiomer simultaneously |
| CN113337855A (en) * | 2021-05-24 | 2021-09-03 | 常州大学 | Filling material and preparation method thereof, and preparation method of electrolytic copper foil for high-frequency signal transmission |
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| CN103940871A (en) * | 2014-04-22 | 2014-07-23 | 同济大学 | Photoelectrocatalysis chiral recognition method of amino acid enantiomer |
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| CN103940871A (en) * | 2014-04-22 | 2014-07-23 | 同济大学 | Photoelectrocatalysis chiral recognition method of amino acid enantiomer |
Non-Patent Citations (2)
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| YONG KONG 等: "SEPARATION OF TRYPTOPHAN ENANTIOMERS WITH POLYPYRROLE ELECTRODE COLUMN BY POTENTIAL-INDUCED TECHNIQUE", 《ELECTROCHIMICA ACTA》 * |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106928434A (en) * | 2017-03-07 | 2017-07-07 | 常州大学 | A kind of method and its application by the tartrate ion synthesis of chiral conducting polymer that adulterates |
| CN107121470A (en) * | 2017-05-08 | 2017-09-01 | 常州大学 | The preparation of molecular engram overoxidised polypyrrole/manganese dioxide/carbon felt composite material |
| CN107219277A (en) * | 2017-05-08 | 2017-09-29 | 常州大学 | The preparation of molecular engram overoxidised polypyrrole/poly- p-aminobenzene sulfonic acid modified electrode |
| CN107121470B (en) * | 2017-05-08 | 2019-05-28 | 常州大学 | The preparation of molecular engram overoxidised polypyrrole/manganese dioxide/carbon felt composite material |
| CN107219277B (en) * | 2017-05-08 | 2019-05-31 | 常州大学 | The preparation of molecular engram overoxidised polypyrrole/poly- p-aminobenzene sulfonic acid modified electrode |
| CN110243902A (en) * | 2019-02-25 | 2019-09-17 | 常州大学 | A kind of bimolecular trace silica/Pt/Polypyrrole composite material preparation method that can identify alanine and tyrosine enantiomer simultaneously |
| CN113337855A (en) * | 2021-05-24 | 2021-09-03 | 常州大学 | Filling material and preparation method thereof, and preparation method of electrolytic copper foil for high-frequency signal transmission |
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