CN106890479A - A kind of preparation method of difunctional affine organic polymer matrix capillary monolithic column - Google Patents
A kind of preparation method of difunctional affine organic polymer matrix capillary monolithic column Download PDFInfo
- Publication number
- CN106890479A CN106890479A CN201710130464.8A CN201710130464A CN106890479A CN 106890479 A CN106890479 A CN 106890479A CN 201710130464 A CN201710130464 A CN 201710130464A CN 106890479 A CN106890479 A CN 106890479A
- Authority
- CN
- China
- Prior art keywords
- acid groups
- monomer
- preparation
- phosphorous acid
- difunctional
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
- B01D15/22—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to the construction of the column
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
- B01D15/20—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to the conditioning of the sorbent material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/38—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 - B01D15/36
- B01D15/3804—Affinity chromatography
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
- B01J20/282—Porous sorbents
- B01J20/285—Porous sorbents based on polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Abstract
The invention discloses a kind of preparation method of difunctional affine organic polymer matrix capillary monolithic column.By the monomer of boracic acid groups, the monomer of phosphorous acid groups, crosslinking agent, pore-foaming agent, initiator, ultrasound, to being completely dissolved, is reinjected in the quartz capillary through vinyl modified the method at room temperature, and capillary monolithic column is obtained by treatment.Polymer substrate capillary monolithic column obtained in the method can be by converting the mobile phase of different condition, realization can both be enriched with glycoprotein on same root post, again can be with enriched phosphorus acidified protein, it is adaptable to separate or small molecule of the enrichment containing 1,2 syn diol structures, glycoprotein and phosphorylated protein.
Description
Technical field
The invention belongs to the preparation field of capillary monolithic column, relate more specifically to a kind of difunctional affine organic polymer base
The preparation method of matter capillary monolithic column.
Background technology
Protein is the executor of physiological function, and one of focus of current life science is proteomics, wherein
Posttranslational modification protein science accounts for critical role in the research of proteomics.Repaiied after glycosylation and phosphorylating protein translation
Decorations are most common posttranslational modifications.Although glycosylation and phosphorylating protein species are various, most targets in biological sample
The relative abundance of glycoprotein and phosphorylated protein is relatively low.Therefore, the primary work of research glycosylation and phosphorylating protein is exactly
How by its from complex system separation and concentration out, this be also posttranslational modification proteomics development key technology.
Capillary monolithic column is the hot research object of micro- separation field, is the bar-shaped fixation of entirety with loose structure
Phase, its advantage is that to prepare simple, mild condition, permeability good, easily modified etc., is gradually sent out in complex biological sample separation field
Wave important function.Integral post can be divided into three parts by the difference of matrix：Inorganic matrix integral post, organic substrate integral post and have
Machine-inorganic hybridization integral post.Organic substrate integral post be mainly by monomer, crosslinking agent, pore-foaming agent, initiator etc. it is well mixed after
In the modified capillary of injection, a period of time is reacted under the conditions of uniform temperature, form polymer continuous bed.Organic substrate is whole
Scapus has the advantages that simple synthetic method, chromatographic performance stabilization, bio-compatibility are good.
Boric acid affinity chromatography is a kind of classical glycoprotein beneficiation technologies（Zian Lin, Jilei Pang, Huanghao
Yang, Zongwei Cai, Lan Zhang, Guonan Chen, Chem. Commun., 2011, 47 (34),
9675-9677.）.Boric acid base group can occur reversible covalent bonds and combine with the material containing 1,2- cis-form dihydroxies in the basic conditions,
Covalent bond dissociation in acid condition discharges the material containing cis-form dihydroxy again.Due to borate affinity chromatography have it is affine
Power is strong, and process is reversible, the advantages of easy to operate, separated in glycoprotein and receives more and more extensive concern with enrichment field.
The selective enrichment of Phosphorylated Peptide is typically to use fixing metal ions affinity chromatography（IMAC）.Traditional IMAC is
Fe3+Or Ga3+Deng with iminodiacetic acid（IDA）Or complexon I（NTA）Chelation is formed, however, this method is not
Enriching phosphated peptide is only capable of, and the acid peptide fragment to non-phosphorylating and the polypeptide containing histidine residues also have certain parent
And effect, it will suppress the enrichment of Phosphorylated Peptide.Zou Hanfa seminars（Shun Feng, Mingliang Ye, Houjiang
Zhou, Xiaogang Jiang, Xingning Jiang, Hanfa Zou, Bolin Gong,
Mol.Cell.Proteomics, 2007, 6:1656-1665）Develop a kind of new with phosphate group as coordinating group
IMAC technologies, by phosphate group by being covalently bound on carrier, then by Ti4+Or Zr4+It is immobilized to carrier surface, use
In selective enrichment phosphorylated protein.
Difunctional affine organic polymer matrix capillary monolithic column has the excellent of Sync enrichment glycoprotein and phosphorylated protein
Point, and high mechanical strength, good penetrability, for the enrichment of glycoprotein and phosphorylated protein provides new method.
The content of the invention
It is an object of the invention in view of the shortcomings of the prior art, providing a kind of based on difunctional affine organic polymer matrix hair
The preparation method of tubule integral post.It is rich that integral post prepared by the method can be respectively used to two kinds of separation of posttranslational modification protein
Collection, with uniform continuous layer fixing phase, good mechanical stability and permeability；It is small with 1,2- cis-form dihydroxies separating
Molecule, glycoprotein and phosphorylated protein aspect have preferably application.
To achieve the above object, the present invention is adopted the following technical scheme that：
A kind of preparation method of difunctional affine organic polymer matrix capillary monolithic column, comprises the following steps：
1）The monomer of boracic acid groups, the monomer of phosphorous acid groups, crosslinking agent, pore-foaming agent and initiator are well mixed, by institute
Mixture sonic oscillation at room temperature is obtained, then leads to nitrogen（Nitrogen blows）To remove the oxygen dissolved in mixture；
2）By step 1）Obtained mixture is injected through in the quartz capillary of vinyl modified, being placed in water-bath after sealing,
And in 60 ~ 85 DEG C（It is preferred that 75 DEG C）12 ~ 24h of generation Raolical polymerizable in situ（It is preferred that 24h）, by capillary from water-bath
The difunctional affine organic polymer matrix capillary that taking-up methyl alcohol or acetonitrile rinse the radical polymerization in situ for being obtained described is whole
Scapus.
The step of the method 1）Described in the monomer of boracic acid groups be any boracic acid groups and terminal olefin simultaneously
Compound, preferably 4- vinylphenylboronic acids；The monomer of phosphorous acid groups is any while the change of phosphorous acid groups and terminal olefin
Compound, preferred vinyl phosphonic acids；Crosslinking agent is ethylene glycol dimethacrylate, pentaerythritol triacrylate or polyethylene glycol
One kind in dimethylacrylate, preferably described crosslinking agent is ethylene glycol dimethacrylate；Pore-foaming agent be diethylene glycol (DEG) and
The mixture of ethylene glycol, initiator is azodiisobutyronitrile.
The monomer of the boracic acid groups is 1 ~ 2 with the molal weight ratio of the monomer of phosphorous acid groups:1, preferably 1:1；Contain
The monomer of boric acid base group is 11 ~ 12 with the mass ratio of crosslinking agent with the gross mass of the monomer of phosphorous acid groups:8 ~ 9, preferably 11.3:
8.7；The mass ratio of the monomer, the monomer of phosphorous acid groups and crosslinking agent three sum and pore-foaming agent of the boracic acid groups is 20
~40:60 ~ 80, preferably 20:80；In the mixture of pore-foaming agent diethylene glycol (DEG) and ethylene glycol, diethylene glycol (DEG) is 60 with the mass ratio of ethylene glycol
~80:1 ~ 20, preferably 72:8；The quality of the initiator is monomer, the monomer and crosslinking agent of phosphorous acid groups of boracic acid groups
The 1 ~ 2% of three's gross mass, preferably 1%.
The present invention is also protected using difunctional affine organic polymer matrix capillary entirety obtained in above-mentioned preparation method
The application of post, obtained capillary monolithic column is for separating or being enriched with the small molecule containing 1,2- cis-form dihydroxy structures, biology is big
Glycoproteins and phosphorylated protein.
Advantages of the present invention is as follows：
1. the difunctional affine organic polymer matrix capillary monolithic column preparation method that the present invention is provided, reaction temperature is gentle, system
Standby process is simple, it is easy to operate.Obtained capillary monolithic column has good fixed bed, and permeability is good, can meet quick, height
Imitate separate requirement；
2. the difunctional affine organic polymer matrix capillary monolithic column that the present invention is provided can meet syn diol structure containing 1,2-
The material such as small molecule, glycoprotein and phosphorylated protein separation or enrichment, it is whole at same with efficient selectivity
The different protein of enrichment is individually separated on scapus.
Brief description of the drawings
Fig. 1 is the scanning electron microscope (SEM) photograph of difunctional affinity capillary entirety column section of the invention；
Fig. 2 is the scanning electron microscope (SEM) photograph of integral post cylinder shown in Fig. 1 and inside pipe wall junction；
Fig. 3 is the chromatographic fractionation figure of catechol and hydroquinones aggregate sample in embodiment 2；
Fig. 4 is bovine serum albumin(BSA) in embodiment 3（BSA）, HRPO（HRP, a kind of glycoprotein）Two kinds of colors of albumen
Spectrum separates figure；
Fig. 5 is bovine serum albumin(BSA) in embodiment 4（BSA）, hemoglobin（Hb）And beta-casein（A kind of phosphorylated protein）Three
Plant the chromatographic fractionation figure of albumen.
Specific embodiment
Technical scheme is described further below by specific embodiment, but the present invention is not limited only to
This.The raw material that the present invention is used can be bought in market, or can be synthesized with methods known in the art.
Embodiment 1
1. pillar pretreatment
Capillary tube inner wall is used acetone rinsing 30min successively, secondary water rinses 1h, and 1.0mol/L sodium hydroxide solutions rinse 12h,
Secondary water rinses 1h, and 0.2mol/L hydrochloric acid solutions rinse 3h, and secondary water rinses 1h, and methyl alcohol rinses 30min, blown in 60 DEG C of nitrogen
It is dry.
2. silanization
Absolute methanol and methyl allyl acyloxypropyl trimethoxysilane are injected in pretreated capillary（γ-MAPS）Body
Product is than being 1：1 mixed liquor, reacts 24h at 45 DEG C, then rinses 30min with methyl alcohol, in 60 DEG C of nitrogen dryings.
3. synthesis in post
Accurately weigh 32.5 mg 4- vinylphenylboronic acids（VPBA）, 24 mg vinyl phosphonates（VPA）, the isobutyl of 1 mg azos two
Nitrile（AIBN）In centrifuge tube, 322 μ L diethylene glycol (DEG)s, 36 μ L ethylene glycol and 42 μ L ethylene glycol dimethacrylates are added
（EDMA）, ultrasonic 20 min at room temperature, until mixture is completely dissolved.Inject the mixture into 100 μm of internal diameters after silanization
In capillary, to 25 cm, sealing two ends react 24 h in being put into 75 DEG C of water-baths.Reaction is taken out after terminating and is cooled to room temperature,
With high pressure constant flow pump, 100% methyl alcohol rinses 40 min to remove unreacted function monomer and react what is produced at low flow rates
Some accessory substances, are obtained difunctional affine organic polymer matrix capillary monolithic column.The integral post is using 100 mmol/ using preceding
L acetic acid rinses 30 min of balance.
The cylinder microscopic appearance of the above-mentioned integral post for preparing is observed with SEM, can learn that material has
There are micron-sized through hole and continuous three-dimensional framework, as shown in Figure 1.
The cylinder microscopic appearance of the above-mentioned integral post for preparing is observed with SEM, integral post can be learnt
Matrix is bonded intact with quartz capillary inwall, 16 MPas of pump pressure is resistant to, with preferable mechanical stability, such as Fig. 2 institutes
Show.
Embodiment 2
In micro column liquid chromatography（μHPLC）Under pattern, with pH 8.0, the mmol/L phosphate solutions of ion concentration 20：Acetonitrile（50/
50, v/v）Buffer solution be mobile phase A, run time 7min；With 100 mmol/L acetums：Acetonitrile（50/50, v/v）'s
Buffer solution is Mobile phase B, and run time is since 7min；Flow rate pump is 0.05 mL/min；Detection wavelength is 214 nm.With
As a example by 1000 μ g/mL catechols and 1000 μ g/mL hydroquinones, under the conditions of mobile phase A, hydroquinones is in integral post
Do not retain and directly be eluted out, and contain 1, the catechol of 2- cis-structures with boric acid base group because forming reversible covalent bonds
It is attracted on post, under the conditions of mobile phase is switched to B, catechol is eluted.The two mixture is obtained in embodiment 1
Difunctional affine organic polymer matrix capillary monolithic column on realize the separation of efficient selective, its chromatographic fractionation figure such as Fig. 3
It is shown.
Embodiment 3
In micro column liquid chromatography（μHPLC）Under pattern, with pH9.0, the mmol/L PBSs of ion concentration 20：0.4
Mol/L sodium chloride（NaCl）（50/50, v/v）Mixed solution be mobile phase A, the min of run time 7；With 100 mmol/L vinegar
Acid solution is Mobile phase B, and run time is since 7 min；Flow rate pump is 0.05 mL/min；Detection wavelength is 214 nm.With non-
Glycoprotein（1000 μ g/mL bovine serum albumin(BSA)s, BSA）With the glycoprotein containing 1,2- cis-structures（1000 μ g/mL horseradish peroxides
Change enzyme, HRP）As a example by, under the conditions of mobile phase A, BSA does not retain in integral post and directly is eluted out, and the sugar on HRP
Chain is attracted on post because forming reversible covalent bonds with boric acid base group, and under the conditions of mobile phase is switched to B, HRP is eluted.
The two protein mixture realizes efficiently choosing on obtained difunctional affine organic polymer matrix capillary monolithic column in embodiment 1
The separation of selecting property, its chromatographic fractionation figure is as shown in Figure 4.
Embodiment 4
Obtained difunctional affine organic polymer matrix capillary monolithic column first uses 10 mmol/L using preceding in embodiment 1
ZrCl4Overnight processed with 0.005 mL/min flow velocitys, make the phosphate group and Zr on integral post skeleton surface4+Chela and effect are formed,
Remaining Zr4+Binding site in acid condition with phosphorylated protein formed chela and, for adsorbing phosphorylated protein, Ran Hou
It is desorbed under alkalescence condition.
In micro column liquid chromatography（μHPLC）Under pattern, with 10 mmol/L, the 3- N-morpholinyls of pH6.0（MOPS）For
Mobile phase A, run time 7min；It is Mobile phase B with 10% ammoniacal liquor, run time is since 7 min；Flow rate pump is 0.05 mL/
min；Detection wavelength is 280 nm.By taking non-phosphorylating protein B SA and Hb and phosphorylated protein beta-casein as an example, protein concentration
1000 μ g/mL are, under the conditions of mobile phase A, non-phosphorylating protein B SA and Hb do not retain in integral post and directly washed
Take off, and phosphorylated protein beta-casein Zr in acid condition in integral post4+Form chelation；When mobile phase switching
To under the conditions of B, beta-casein is eluted.Obtained difunctional affinity capillary is whole in embodiment 1 for the two protein mixture
The separation of efficient selective is realized on scapus, its chromatographic fractionation figure is as shown in Figure 5.
The foregoing is only presently preferred embodiments of the present invention, all impartial changes done according to scope of the present invention patent with
Modification, should all belong to covering scope of the invention.
Claims (10)
1. a kind of preparation method of difunctional affine organic polymer matrix capillary monolithic column, it is characterised in that：Methods described bag
Include following steps：
1）The monomer of boracic acid groups, the monomer of phosphorous acid groups, crosslinking agent, pore-foaming agent and initiator are well mixed, by institute
Mixture sonic oscillation at room temperature is obtained, then leads to nitrogen to remove the oxygen dissolved in mixture；
2）By step 1）Obtained mixture injection occurs through in the quartz capillary of vinyl modified, sealing is placed in water-bath
Raolical polymerizable in situ；Capillary is taken out from water-bath, is rinsed with methyl alcohol or acetonitrile and described original position is obtained freely
The difunctional affine organic polymer matrix capillary monolithic column of base polymerization.
2. preparation method according to claim 1, it is characterised in that：Step 1）In, the monomer of the boracic acid groups is
While the one kind in the compound of boracic acid groups and terminal olefin, the monomer of phosphorous acid groups is for while phosphorous acid groups and end
One kind in the compound of terminal olefine.
3. preparation method according to claim 1, it is characterised in that：Step 1）In, the crosslinking agent is glycol dinitrate
One kind in base acrylate, pentaerythritol triacrylate and polyethylene glycol dimethacrylate；Pore-foaming agent is diethylene glycol (DEG)
With the mixture of ethylene glycol；Initiator is azodiisobutyronitrile.
4. preparation method according to claim 3, it is characterised in that：In the pore-foaming agent, the matter of diethylene glycol (DEG) and ethylene glycol
Amount is than being 60 ~ 80:1~20.
5. preparation method according to claim 4, it is characterised in that：The diethylene glycol (DEG) is 72 with the mass ratio of ethylene glycol:
8。
6. preparation method according to claim 1, it is characterised in that：The step 1）In, the monomer of boracic acid groups with
The molal weight ratio of the monomer of phosphorous acid groups is 1 ~ 2:1；Total matter of the monomer of boracic acid groups and the monomer of phosphorous acid groups
Amount is 11 ~ 12 with the mass ratio of crosslinking agent:8~9；The monomer of boracic acid groups, the monomer of phosphorous acid groups and crosslinking agent three it
And with the mass ratio of pore-foaming agent be 20 ~ 40:60~80；The quality of the initiator is monomer, the phosphorous acid groups of boracic acid groups
Monomer and crosslinking agent three's gross mass 1 ~ 2%.
7. preparation method according to claim 6, it is characterised in that：The monomer of the boracic acid groups and phosphorous acid groups
Monomer molal weight ratio be 1:1；The monomer of the boracic acid groups and the gross mass of the monomer of phosphorous acid groups and crosslinking
The mass ratio of agent is 11.3:8.7；The monomer of the boracic acid groups, the monomer of phosphorous acid groups and crosslinking agent three sum with
The mass ratio of pore-foaming agent is 20:80；The quality of the initiator is monomer, the monomer of phosphorous acid groups and the friendship of boracic acid groups
The 1% of connection agent three's gross mass.
8. preparation method according to claim 1, it is characterised in that：The step 2）In, reaction temperature is 60 ~ 85 DEG C；
Reaction time is 12 ~ 24h.
9. preparation method according to claim 8, it is characterised in that：The step 2）In, reaction temperature is 75 DEG C；Reaction
Time is 24h.
10. difunctional affine organic polymer matrix capillary obtained in the preparation method according to any one of claim 1 ~ 9
The application of pipe integral post, it is characterised in that：Obtained difunctional affine organic polymer matrix capillary monolithic column be used for separate or
It is enriched with small molecule, large biological molecule glycoprotein and the phosphorylated protein of the structure of cis-form dihydroxy containing 1,2-.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710130464.8A CN106890479B (en) | 2017-03-07 | 2017-03-07 | A kind of preparation method of difunctional affine organic polymer matrix capillary monolithic column |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710130464.8A CN106890479B (en) | 2017-03-07 | 2017-03-07 | A kind of preparation method of difunctional affine organic polymer matrix capillary monolithic column |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106890479A true CN106890479A (en) | 2017-06-27 |
| CN106890479B CN106890479B (en) | 2019-04-02 |
Family
ID=59185508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710130464.8A Active CN106890479B (en) | 2017-03-07 | 2017-03-07 | A kind of preparation method of difunctional affine organic polymer matrix capillary monolithic column |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106890479B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109433168A (en) * | 2018-12-24 | 2019-03-08 | 天津医科大学 | Catechol trace capillary monolithic column of boron affinity interaction and preparation method thereof |
| CN115197465A (en) * | 2022-07-27 | 2022-10-18 | 佛山科学技术学院 | Preparation method and application of betulinic acid polymer monolithic column |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105536293A (en) * | 2016-01-15 | 2016-05-04 | 福州大学 | Boronic acid affinity organic silica gel hybrid monolithic column and preparation method thereof |
| CN105646750A (en) * | 2014-12-02 | 2016-06-08 | 中国科学院大连化学物理研究所 | Method for preparation of organic porous monolithic material based on photoinduced thiol-ene polymerization |
-
2017
- 2017-03-07 CN CN201710130464.8A patent/CN106890479B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105646750A (en) * | 2014-12-02 | 2016-06-08 | 中国科学院大连化学物理研究所 | Method for preparation of organic porous monolithic material based on photoinduced thiol-ene polymerization |
| CN105536293A (en) * | 2016-01-15 | 2016-05-04 | 福州大学 | Boronic acid affinity organic silica gel hybrid monolithic column and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 俞瑞芳: "几种新型有机聚合基质毛细管整体柱的制备及应用研究", 《CNKI优秀硕士学位论文全文库》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109433168A (en) * | 2018-12-24 | 2019-03-08 | 天津医科大学 | Catechol trace capillary monolithic column of boron affinity interaction and preparation method thereof |
| CN115197465A (en) * | 2022-07-27 | 2022-10-18 | 佛山科学技术学院 | Preparation method and application of betulinic acid polymer monolithic column |
| CN115197465B (en) * | 2022-07-27 | 2023-05-30 | 佛山科学技术学院 | Preparation method and application of betulinic acid polymer monolithic column |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106890479B (en) | 2019-04-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU678446B2 (en) | Compositions and methods for protein structural determinations | |
| JPH032560A (en) | Fixed carrier for novel chromatography | |
| Zhang et al. | Chiral porous organic frameworks and their application in enantioseparation | |
| JPH03502836A (en) | fixed artificial membrane | |
| CN107163130B (en) | Angiotensin converting enzyme inhibitory peptide and preparation and extraction method thereof | |
| CN102068965B (en) | Method for preparing chitosan separation medium suitable for protein purification | |
| CN105131329B (en) | A kind of preparation method and application of the polyvinyl alcohol crosslinked affinity membrane of macropore chitosan of chelated metal ions | |
| CN106890479A (en) | A kind of preparation method of difunctional affine organic polymer matrix capillary monolithic column | |
| CN102947327A (en) | Purification of caspofungin intermediates | |
| CA2708291A1 (en) | Production of recombinant interferon proteins | |
| CN103102388A (en) | Method for sequentially enriching multi-phosphopeptide and mono-phosphopeptide | |
| CN108079954B (en) | Functionalized graphene oxide composite nanomaterial and preparation and application thereof | |
| CN102760543A (en) | Hydrophilic metal ion immobilization affinity magnetic bead and preparation and application thereof | |
| CN102059157B (en) | Anion exchange integral material as well as conventional liquid phase chromatographic column or quartz capillary column taking anion exchange integral material as separating medium and preparation method thereof | |
| Ba et al. | Construction of dual-hydrophilic metal-organic framework with hierarchical porous structure for efficient glycopeptide enrichment | |
| CN105561958A (en) | Ionic liquid bonded silica gel for enrichment and purification of shellfish toxins and preparation method thereof | |
| CN111617743B (en) | Zeolite imidazolate framework material ANA- [ Co (eIm) 2 ]Preparation method and application of | |
| US6441146B1 (en) | Affinity immobilized metal resins | |
| Jubb et al. | Redox chemistry of meso-octaethylporphyrinogen: formation and opening of a cyclopropane ring | |
| CN1325511C (en) | Glutathion purification and separation method | |
| CN101185881A (en) | Chromatogram medium for immunoglobulin class protein separation purification and preparation method thereof | |
| CN101284224B (en) | Expanded bed adsorption medium with sulfhydryl ethylpyridine and sulfone group as ligand separation antibody and preparation method | |
| WO2020195303A1 (en) | Peptide complex and production method therefor, and use of said peptide complex | |
| CN1752105A (en) | Biomimetic affinity purification method of vitellus immune globulin | |
| CN101279244B (en) | Hydrophobic electric charge induced type thiophil expanded adsorbent bed medium and method for producing the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |