CN107999026A - Affinity chromatography medium using asparagine as functional ligand - Google Patents
Affinity chromatography medium using asparagine as functional ligand Download PDFInfo
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- CN107999026A CN107999026A CN201711278688.XA CN201711278688A CN107999026A CN 107999026 A CN107999026 A CN 107999026A CN 201711278688 A CN201711278688 A CN 201711278688A CN 107999026 A CN107999026 A CN 107999026A
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- asparagine
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- 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
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/14—Extraction; Separation; Purification
- C07K1/16—Extraction; Separation; Purification by chromatography
- C07K1/22—Affinity chromatography or related techniques based upon selective absorption processes
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- Proteomics, Peptides & Aminoacids (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Peptides Or Proteins (AREA)
Abstract
This case is related to a kind of affinity chromatography medium using asparagine as functional ligand, including chromatography substrate, space arm and aglucon, and the chromatography substrate is macropore beta cyclodextrin microballoon, and space arm is 6 amion acetic acids, and aglucon is asparagine.The peptide chain of asparagine aglucon of the present invention is shorter, and cost is relatively low, and coupling is convenient, efficient；Asparagine aglucon has salt tolerant characterization of adsorption, without salt treatment is diluted or added to feed liquid；Elution requirement is gentle, can avoid peracid or cross the elution requirements such as alkali to protein structure generation harmful effect or loss of activity, therefore with good antibody separation application prospect.
Description
Technical field
The present invention relates to a kind of using asparagine as chromatography media of functional ligand and preparation method thereof, belong to biochemical industry
Protein chromatographic isolation technics in field.
Background technology
Antibody can be specifically bound with corresponding antigens, produce various immunological effects.With biotechnology fast development and
Antibody engineering technology is constantly broken through, and monoclonal antibody, polyclonal antibody and genetic engineering antibody have been widely used for biology
And medical domain.Antibody purposes mainly includes disease treatment, in-vitro diagnosis and detection, tumor-localizing imaging and as affine
Aglucon is used to isolate and purify.
Often purity requirement is higher for antibody product, while must also keep bioactivity, therefore traditional separation process is past
It is past to be difficult to meet the requirements.Albumin A or protein g affinity chromatography medium can specifically bind antibody, but protide affinity ligand is easy
Come off by proteasome degradation in feed liquid, polluted product, and reuse number is low, medium is expensive, and running cost is high, limit
Its large-scale application is made.Although and the methods of traditional ion-exchange chromatography and hydrophobic interaction chromatography can combine it is anti-
Body, but specific and selectivity is poor, separating step is more, and purification effect is limited.Therefore, exploitation is with the non-of antibody selectivity
Protide aglucon becomes research hotspot.
The content of the invention
For above-mentioned shortcoming, it is an object of the invention to provide a kind of affine layer using asparagine as functional ligand
Analyse medium.
A kind of affinity chromatography medium using asparagine as functional ligand, wherein, including chromatography substrate, space arm and match somebody with somebody
Base, the chromatography substrate are macropore beta-cyclodextrin microballoon, and space arm is 6-ACA 6-aminocaproic acid, and aglucon is asparagine.
Preferably, the preparation method using asparagine as the affinity chromatography medium of functional ligand, wherein, including
Following steps：
1) after chromatography substrate is drained, add 0.3-1 times of chromatography substrate quality percent by volume be 30% acetone,
The allyl chloride of 0.8-1.6 times of chromatography substrate quality and the sodium hydroxide of 0.1-1 times of chromatography substrate quality, 200rpm shakes at 40 DEG C
When activation 30-50 is small in bed, filter, be washed with deionized to obtain activation chromatography substrate；
2) chromatography substrate will be activated and the 0.2-0.8 times of N- chlorosuccinimide for activating chromatography substrate quality is mixed and carried out
Chloro refines, and when reaction 2 is small in 200rpm shaking tables at 50 DEG C, filters, is washed with deionized, obtains the chromatography base of chloro alcoholization
Matter；
3) by the 6-ACA 6-aminocaproic acid of the chromatography substrate of chloro alcoholization and the chromatography substrate quality of 0.4-1 times of chloro alcoholization and
1M sodium carbonate buffers mix, and when reaction 5-20 is small in 200rpm shaking tables at 40 DEG C, obtain activated carboxylic matrix；
4) activated carboxylic matrix is taken, is cleaned respectively with deionized water, absolute ethyl alcohol and dry N-methylpyrrolidone, is cleaned
Activated carboxylic matrix afterwards is added to the asparagine containing 0.5-2 times of activated carboxyl density, 0.2-3 times of activated carboxyl density
2- (7- azos benzotriazole)-N, N, N', N'- tetramethylurea hexafluorophosphoric acids ester, the N- isopropyls of 0.2-5 times of activated carboxyl density
In the 1-methyl-2-pyrrolidinone solution of base methylamine, when reaction 4-10 is small in shaking bath at 25 DEG C, after obtaining asparagine coupling
Medium；
5) medium after asparagine is coupled is cleaned with dry N-methylpyrrolidone, acetone and deionized water successively,
Filter, be added in the mixed liquor of sodium acetate and acetic anhydride, when reaction 2 is small in shaking bath at 25 DEG C, deionized water washing, obtains
To the affinity chromatography medium using asparagine as functional group.
Preferably, the preparation method, wherein, the volume ratio of the sodium acetate and acetic anhydride is 2:1.
Preferably, the preparation method, wherein, the pH of the sodium carbonate buffer is 10-12.
Preferably, the affinity chromatography medium using asparagine as functional ligand, wherein, the allyl chloride and
The mass ratio of chromatography substrate is 0.7-1.6：1.
The beneficial effects of the invention are as follows：
The affinity chromatography medium using asparagine as functional ligand that the present invention develops, it is auxiliary that ligand structure is based on molecular simulation
Design is helped, it is similar with the pattern of the natural ligand binding antibody such as albumin A, there is good affinity and selectivity to antibody, it is main
Feature is wanted to be embodied in：(1) antibody adsorption capacity is big, the saturated capacity of Static Adsorption up to 100mg/g humid mediums more than；(2) have
There is the characteristic that salt tolerant adsorbs, in wider salt concentration range (0-1M NaCl), high-adsorption-capacity can be kept；(3) carboxyl is lived
It is gentle to change reaction condition, it is of low cost；(4) asparagine ligand cou is efficient, and density is controllable；(5) using 6-ACA 6-aminocaproic acid as
Space arm, asparagine aglucon can be fully extended to duct space, be conducive to antibody binding；(6) medium character is stablized, cleaning
Regeneration is convenient.The key of the present invention is that the peptide chain of asparagine aglucon is shorter, and cost is relatively low, and coupling is convenient, efficient；Asparagus fern
Acid amides aglucon has salt tolerant characterization of adsorption, without salt treatment is diluted or added to feed liquid；Elution requirement is gentle, can avoid peracid
Or cross the elution requirement such as alkali and produce harmful effect or loss of activity to protein structure, therefore with good antibody separation application before
Scape.
Embodiment
With reference to embodiment, the present invention is described in further detail, to make those skilled in the art with reference to specification
Word can be implemented according to this.
Embodiment 1
Macropore beta-cyclodextrin microballoon 10g is taken, the percent by volume for adding 3g is 30% acetone, the allyl chloride and 2g of 8g
Sodium hydroxide, when activation 30 is small in 200rpm shaking tables at 40 DEG C, filter, be washed with deionized to obtain activation chromatography substrate；
The N- chlorosuccinimides for activating chromatography substrate and 2g are mixed and carry out chlorhydrin, react 2 in 200rpm shaking tables at 50 DEG C
Hour, filter, be washed with deionized, obtain the chromatography substrate of chloro alcoholization；By the chromatography substrate of chloro alcoholization and the 6- of 5g
Amion acetic acid and the mixing of 1M sodium carbonate buffers, the pH of sodium carbonate buffer are to react 10 in 200rpm shaking tables at 12,40 DEG C
Hour, obtain activated carboxylic matrix；Activated carboxylic matrix is taken, respectively with deionized water, absolute ethyl alcohol and anhydrous N-methyl pyrroles
Alkanone is cleaned, and the activated carboxylic matrix after cleaning is added to 2- (three nitrogen of 7- azos benzo of the asparagine containing 6g, 10g
Azoles)-N, N, N', N'- tetramethylurea hexafluorophosphoric acids ester, 2g N-methylisopropylamine 1-methyl-2-pyrrolidinone solution in, 25 DEG C
When reaction 5 is small in lower shaking bath, the medium after asparagine coupling is obtained；Medium after asparagine is coupled uses nothing successively
Water 1-methyl-2-pyrrolidinone, acetone and deionized water cleaning, filter, are added in the mixed liquor of sodium acetate and acetic anhydride, acetic acid
The volume ratio of sodium and acetic anhydride is 2:When reaction 2 is small in shaking bath at 1,25 DEG C, deionized water washing, obtains with asparagine
For the affinity chromatography medium of functional group, ligand density is 60 μm of ol/mL.
Embodiment 2
Take macropore beta-cyclodextrin microballoon 10g, add 5g percent by volume be 30% acetone, 10g allyl chloride and
The sodium hydroxide of 3g, when activation 35 is small in 200rpm shaking tables at 40 DEG C, filters, and is washed with deionized to obtain activation chromatography base
Matter；The N- chlorosuccinimides for activating chromatography substrate and 4g are mixed and carry out chlorhydrin, it is anti-in 200rpm shaking tables at 50 DEG C
Answer 2 it is small when, filter, be washed with deionized, obtain chloro alcoholization chromatography substrate；By the chromatography substrate and 6g of chloro alcoholization
6-ACA 6-aminocaproic acid and the mixing of 1M sodium carbonate buffers, the pH of sodium carbonate buffer are to be reacted at 12,40 DEG C in 200rpm shaking tables
12 it is small when, obtain activated carboxylic matrix；Activated carboxylic matrix is taken, respectively with deionized water, absolute ethyl alcohol and anhydrous N-methyl pyrrole
Pyrrolidone cleans, and the activated carboxylic matrix after cleaning is added to 2- (three nitrogen of 7- azos benzo of the asparagine containing 10g, 15g
Azoles)-N, N, N', N'- tetramethylurea hexafluorophosphoric acids ester, 10g N-methylisopropylamine 1-methyl-2-pyrrolidinone solution in, 25 DEG C
When reaction 5 is small in lower shaking bath, the medium after asparagine coupling is obtained；Medium after asparagine is coupled uses nothing successively
Water 1-methyl-2-pyrrolidinone, acetone and deionized water cleaning, filter, are added in the mixed liquor of sodium acetate and acetic anhydride, acetic acid
The volume ratio of sodium and acetic anhydride is 2:When reaction 2 is small in shaking bath at 1,25 DEG C, deionized water washing, obtains with asparagine
For the affinity chromatography medium of functional group, ligand density is 80 μm of ol/mL.
Embodiment 3
Take macropore beta-cyclodextrin microballoon 10g, add 8g percent by volume be 30% acetone, 12g allyl chloride and
The sodium hydroxide of 6g, when activation 40 is small in 200rpm shaking tables at 40 DEG C, filters, and is washed with deionized to obtain activation chromatography base
Matter；The N- chlorosuccinimides for activating chromatography substrate and 6g are mixed and carry out chlorhydrin, it is anti-in 200rpm shaking tables at 50 DEG C
Answer 2 it is small when, filter, be washed with deionized, obtain chloro alcoholization chromatography substrate；The chromatography substrate and 10g that chloro is refined
6-ACA 6-aminocaproic acid and the mixing of 1M sodium carbonate buffers, the pH of sodium carbonate buffer be anti-in 200rpm shaking tables at 12,40 DEG C
When answering 5-20 small, activated carboxylic matrix is obtained；Activated carboxylic matrix is taken, respectively with deionized water, absolute ethyl alcohol and anhydrous N- first
Base pyrrolidones cleans, and the activated carboxylic matrix after cleaning is added to 2- (three nitrogen of 7- azos benzo of the asparagine of 10g, 20g
Azoles)-N, N, N', N'- tetramethylurea hexafluorophosphoric acids ester, 20g N-methylisopropylamine 1-methyl-2-pyrrolidinone solution in, 25 DEG C
When reaction 10 is small in lower shaking bath, the medium after asparagine coupling is obtained；Medium after asparagine is coupled is used successively
Dry N-methylpyrrolidone, acetone and deionized water cleaning, filter, are added in the mixed liquor of sodium acetate and acetic anhydride, second
The volume ratio of sour sodium and acetic anhydride is 2:When reaction 2 is small in shaking bath at 1,25 DEG C, deionized water washing, obtains with asparagus fern acyl
Amine is the affinity chromatography medium of functional group.
Embodiment 4
1 obtained chromatography media of Example tests the Static Adsorptive capacity of human IgG, and it is dense to investigate different NaCl
The influence of degree.First with the abundant cleansing medium of deionized water, and balanced with buffer solution.0.04g media are accurately weighed respectively in 2mL
In centrifuge tube, the buffer solution of 0.8mL different people IgG concentration is added；Centrifuge tube is placed in constant temperature blending instrument, at 25 DEG C
1500rpm adsorbs 2h, after reaching adsorption equilibrium, centrifuges, and takes out the concentration of supernatant measure human IgG；According to material balance
The adsorption capacity of calculation medium, draws adsorption isotherm, and obtains saturated adsorption capacity according to Langmuir equation models and conciliate
From constant.In 0M NaCl conditions, the saturated adsorption capacity to human IgG is affinity chromatography medium prepared by the embodiment of the present invention 1
89.2mg/g media, dissociation constant 0.8mg/mL；In 1M NaCl conditions, saturated adsorption capacity is 63.9mg/g media, solution
It is 0.8mg/mL from constant.The result shows that asparagine affinity chromatography medium is larger to human IgG adsorbance, there is well resistance to
Salt characterization of adsorption.
Embodiment 5
1 obtained chromatography media of Example isolates and purifies monoclonal antibody feed liquid.Medium is through equalizing and buffering
Liquid (30mM sodium phosphate buffers, pH 7.0, NaCl containing 1.5M) fully balances, cell culture fluid loading 10mL；10 cylinders
Equilibration buffer wash is accumulated to baseline；The 20mM sodium-acetate buffers elution of pH 4 or pH 5；Finally carried out with 0.1M NaOH
Situ cleaning.The sample afforded is analyzed with non-reduced SDS-PAGE and HPLC, and monoclonal antibody purity reaches 99.5% and (washes
4) and 99.6% (elution pH is 5) de- pH is.
Although embodiment of the present invention is disclosed as above, it is not restricted in specification and embodiment listed
With it can be applied to various suitable the field of the invention completely, can be easily for those skilled in the art
Realize other modification, therefore under the universal limited without departing substantially from claim and equivalency range, it is of the invention and unlimited
In specific details.
Claims (5)
- A kind of 1. affinity chromatography medium using asparagine as functional ligand, it is characterised in that including chromatography substrate, space arm and Aglucon, the chromatography substrate are macropore beta-cyclodextrin microballoon, and space arm is 6-ACA 6-aminocaproic acid, and aglucon is asparagine.
- 2. a kind of preparation method using asparagine as the affinity chromatography medium of functional ligand as claimed in claim 1, it is special Sign is, includes the following steps：1) after chromatography substrate is drained, the percent by volume for adding 0.3-1 times of chromatography substrate quality is 30% acetone, pi-allyl The sodium hydroxide of chlorine and 0.1-1 times of chromatography substrate quality, activate in 200rpm shaking tables at 40 DEG C 30-50 it is small when, filter, spend from Sub- water washing obtains activation chromatography substrate；2) chromatography substrate will be activated and the 0.2-0.8 times of N- chlorosuccinimide for activating chromatography substrate quality mixes and carry out chloro Refine, when reaction 2 is small in 200rpm shaking tables at 50 DEG C, filters, be washed with deionized, obtain the chromatography substrate of chloro alcoholization；3) by the chromatography substrate of chloro alcoholization and the 6-ACA 6-aminocaproic acid and 1M carbon of the chromatography substrate quality of 0.4-1 times of chloro alcoholization Sour sodium buffer solution mixes, and when reaction 5-20 is small in 200rpm shaking tables at 40 DEG C, obtains activated carboxylic matrix；4) activated carboxylic matrix is taken, is cleaned respectively with deionized water, absolute ethyl alcohol and dry N-methylpyrrolidone, after cleaning Activated carboxylic matrix is added to the asparagine containing 0.5-2 times of activated carboxyl density, the 2- of 0.2-3 times of activated carboxyl density (7- azos benzotriazole)-N, N, N', N'- tetramethylurea hexafluorophosphoric acids ester, the N- isopropyls of 0.2-5 times of activated carboxyl density In the 1-methyl-2-pyrrolidinone solution of methylamine, when reaction 4-10 is small in shaking bath at 25 DEG C, after obtaining asparagine coupling Medium；5) medium after asparagine is coupled is cleaned with dry N-methylpyrrolidone, acetone and deionized water successively, is filtered, Be added in the mixed liquor of sodium acetate and acetic anhydride, at 25 DEG C in shaking bath reaction 2 it is small when, deionized water washing, obtain with Asparagine is the affinity chromatography medium of functional group.
- 3. preparation method as claimed in claim 2, it is characterised in that the sodium acetate and the volume ratio of acetic anhydride are 2:1.
- 4. preparation method as claimed in claim 2, it is characterised in that the pH of the sodium carbonate buffer is 10-12.
- 5. the affinity chromatography medium using asparagine as functional ligand as claimed in claim 1, it is characterised in that the allyl The mass ratio of base chlorine and chromatography substrate is 0.7-1.6：1.
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| CN201711278688.XA CN107999026A (en) | 2017-12-06 | 2017-12-06 | Affinity chromatography medium using asparagine as functional ligand |
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| CN201711278688.XA CN107999026A (en) | 2017-12-06 | 2017-12-06 | Affinity chromatography medium using asparagine as functional ligand |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105821025A (en) * | 2016-04-06 | 2016-08-03 | 浙江丰安生物制药有限公司 | Extraction method of thrombin |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120208295A1 (en) * | 2004-01-13 | 2012-08-16 | Wuxi WeiYi Zhinengkeji, Inc. | Methods and compositions for mass spectrometry analysis |
| CN104645949A (en) * | 2015-02-04 | 2015-05-27 | 浙江大学 | Affinity chromatography medium employing tetrapeptide as functional ligand and preparation method of affinity chromatography medium |
| US20170212128A1 (en) * | 2004-01-13 | 2017-07-27 | Tianxin Wang | Methods and compositions for mass spectrometry analysis |
| CN107243336A (en) * | 2017-06-27 | 2017-10-13 | 大连理工大学 | A kind of chromatography media and its preparation method and application |
-
2017
- 2017-12-06 CN CN201711278688.XA patent/CN107999026A/en not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120208295A1 (en) * | 2004-01-13 | 2012-08-16 | Wuxi WeiYi Zhinengkeji, Inc. | Methods and compositions for mass spectrometry analysis |
| US20170212128A1 (en) * | 2004-01-13 | 2017-07-27 | Tianxin Wang | Methods and compositions for mass spectrometry analysis |
| CN104645949A (en) * | 2015-02-04 | 2015-05-27 | 浙江大学 | Affinity chromatography medium employing tetrapeptide as functional ligand and preparation method of affinity chromatography medium |
| CN107243336A (en) * | 2017-06-27 | 2017-10-13 | 大连理工大学 | A kind of chromatography media and its preparation method and application |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105821025A (en) * | 2016-04-06 | 2016-08-03 | 浙江丰安生物制药有限公司 | Extraction method of thrombin |
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