CN105771943B - The preparation method and applications of bacitracin bonding type chromatograph packing material - Google Patents
The preparation method and applications of bacitracin bonding type chromatograph packing material Download PDFInfo
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- CN105771943B CN105771943B CN201610143020.3A CN201610143020A CN105771943B CN 105771943 B CN105771943 B CN 105771943B CN 201610143020 A CN201610143020 A CN 201610143020A CN 105771943 B CN105771943 B CN 105771943B
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- 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
- B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/50—Aspects relating to the use of sorbent or filter aid materials
- B01J2220/52—Sorbents specially adapted for preparative chromatography
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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
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/50—Aspects relating to the use of sorbent or filter aid materials
- B01J2220/54—Sorbents specially adapted for analytical or investigative chromatography
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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
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/80—Aspects related to sorbents specially adapted for preparative, analytical or investigative chromatography
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Abstract
The present invention provides a kind of cyclic peptide (bacitracin) bonding type chromatograph packing material, contains a large amount of amido bonds.Specifically, fixed phase stuffing provided by the invention has hydrophilic nmature, preparation method is that ring type polypeptide (bacitracin) is bonded on silanized silica gel carrier by organic crosslinking agent.This method is easy to operate, and synthesis cycle is short, and bonding efficiency is high, low in cost, has more excellent stability and reproducibility.Feature of the present invention is the ability containing a variety of functional groups such as amide, amino and carboxyl, with very strong polarity and formation hydrogen bond.Present invention can apply to which all there is good separation selectivity to most polar compounds under the conditions of hydrophilic chromatographic, have the advantages that Column stability is good.
Description
Technical field
The present invention relates to a kind of cyclic peptide bonding type chromatograph packing materials and preparation method thereof, and in particular to passing through organic crosslinking agent
Natural cyclic bacitracin is bonded the chromatograph packing material that obtains on silanization silica-gel carrier, can be applied to various drug chromatography and
Separation, belongs to technical field of chromatography separation.
Background technique
High performance liquid chromatography (HPLC) is widely used in being related to nearly all bases such as medicine, environmental protection, life science
And Applied research fields, now have developed into essential analysis tool.The development of high performance liquid chromatography is with the hair of chromatograph packing material
Based on exhibition, the exploitation of novel liquid-phase chromatograph packing material has highly important significance of scientific research and application value.Reversed-phase liquid chromatography
(RPLC) it is the chromatographic separation technology being most widely used at present, separation is suitble to analyze most of low pole and moderately polarization
Object is closed, still, highly polar and ionic compound often without reserve or retains very weak on RPLC.To solve this problem, one
As in mobile phase be added ion-pairing agent (such as various alkylsulfonates or quaternary ammonium salt) to realize highly polar or ionic
The separation of object is closed, but ion-pairing agent belongs to non-volatile salt, it cannot be with the LC-MS technology of highly sensitive high specificity
(LC-MS) it matches.Although mobile phase is that the normal-phase chromatography (NPLC) of nonpolar solvent can also analyze highly polar compound,
NPLC is also incompatible with LC-MS, this is because interface of the nonpolar liquid phase of NPLC in LC-MS can not make measured object ion
Change；In addition, NPLC can also have the poor equal other problems of certain analytes dissolubility in nonpolar liquid phase.So real
It is always now that chromatography worker wants the problem in science solved to the LC-MS analysis of highly polar compound.
The appearance of hydrophilic Interaction Chromatography technology (HILIC) property offer the possibility to solve the above problem.HILIC technology uses
60%) and the binary washing and dehydrating integrated machine conduct of a small amount of water phase composition by a high proportion of organic phase, (predominantly acetonitrile, content are typically larger than
Mobile phase, the mobile phase can preferably evaporate in LC-MS interface and ionize analyte, be highly polar drug, core
The objects Quality Research such as acid and polypeptide provides a preferably chromatography condition.The hydrophilic color of commercialization at present and research report
Composing filling kind includes pure silicon glue, polar group (such as amino, amide, cyano, glycol, polysuccinimide, cyclodextrin, both sexes
Ion) bonded silica gel stationary phase, the HILIC stationary phase of organic polymer matrix, entirety HILIC stationary phase [Ray S, et
Al.Analyst, 2012,137,4907-4909].As Yang Duo et al. is prepared for polypropylene using sulfydryl alkene " click chemistry "
Acid amide type chromatograph packing material, nucleosides, base and oligosaccharides can preferably [Yang Duo waits points for separation in this hydrophilic interaction stationary phase
Analysis chemistry, 2015,43 (10): 1439-1444.].Cellulose is coated in the silica gel material of sulfonation by ionic interaction
On, coating procedure Environmental Safety is all widely used [Sheng Q, et in glycobiology and glycoprotein group
Al.J.Chromatogr.A, 2013,1291:56-63.].Yuan et al. has by the hydrophily that thermal polymerization technology is prepared in situ
(5%, v/v) the hydrophily interaction under low acetonitrile concentration of machine polyalcohol integral pole still remains, hydrophilic interaction section
Greatly [Yuan G, et al.J.Chromatogr.A, 2013,1301:88-97.].Although these hydrophilic chromatographic fillers are to separation pole
Property compound shows good selectivity and splendid reproducibility, but there is also some shortcomings: certain solvents can dissolve
Or the polysaccharide derivates coated in swelling application type chromatographic column, therefore the selection of mobile phase is limited.Although existing bonding type energy
Overcome these weakness, but bonding type hydrophilic chromatographic filler usually has the disadvantages such as reaction step is more, bonding efficiency is low.Integral post
Easily modified, column effect is high, back-pressure is low, mass transfer velocity is fast, but the repeatability in aperture is difficult to ensure, therefore its chromatographic performance difference between batch
It is different larger.In addition to this, the disadvantages of mechanical stability is usually poor, Organic Polymer Monolithic Columns solvent action lower prop expands
Limit further being widely used for integral post.Although HILIC technology development in recent years is very rapid, hydrophilic chromatographic filler
Type is still extremely limited, and further research is worth to be expanded.
Based on above research background, inventor has developed a kind of novel chromatographic stationary phases and preparation method thereof,
Silica Surface carries out certain modification, and bacitracin is bonded to Silica Surface, which has hydrophilic nmature.Bacitracin
(bacitracin, CAS 1405-87-4, molecular structure such as following formula) is a kind of polypeptide antibiotics, molecular weight 1422.69,
It is a kind of polypeptide containing thiazole ring being made of 12 amino acid.There are a variety of functional group pendant's (such as ammonia in bacillus peptide molecule
Base, carboxyl), amido bond enhances hydrophily, and unique composition and orderly cyclic structure are some substances of selective absorption
Multiple action sites are provided, the chromatography retention property different from common stationary phase is inherently shown.Studies have shown that this is fixed
Relatively most polar compounds with all there is good separation selectivity under the matched mobile phase of mass spectrum, can solve strong
Application problem of the polar compound on LC-MS.Advantage of the invention is also manifested by synthetic operation simplicity, with short production cycle.This
Outside, bacitracin belongs to the medicinal raw material that Chinese Pharmacopoeia records, from the horse's mouth, cheap, makes the new chromatographic filler of invention
Preparation cost is lower.So far, there has been no report bacitracin and the silica gel bonded research as chromatograph packing material.
Summary of the invention
The present invention provides a kind of chromatograph stationary-phase stuffing, it is characterised in that: the bar containing amide groups is bonded on silica gel material
Bacterium peptide, the fixed phase stuffing have hydrophilic nmature.
Chromatograph stationary-phase stuffing provided by the invention, it is characterized in that the generally spherical Bio-sil of the silica gel material,
The partial size of spherical porous chromatographic grade silica gel is 1~50 μm, and average pore size is
Fixed phase stuffing provided by the invention, it is characterized in that silica gel material silane coupling agent shown in following formula
Surface treatment:
Wherein, R1~R3 respectively represents saturation with 1~20 carbon atom or unsaturated alkyl or has 1~8 carbon
Atom simultaneously can have one or two carbon atom and can have the saturation or unsaturated hydrocarbons of one or two or more a substituent groups
Base；Y is containing amino, the alkyl with 1~10 carbon atom, alkoxy or azepine-silicyl；And taking of can having of the hydrocarbon
Dai Ji independently represents itrile group, hydroxyl, amino, pyridine or amide groups.
Fixed phase stuffing described in any one according to claim 1~4, it is characterized in that organic crosslinking agent molecule is to divide
With the compound of multiple isocyanate group in son.
The preparation method of fixed phase stuffing provided by the invention, which comprises the following steps:
Step 1, the processing of silica gel material surface amino groups silane coupling agent: taking activation silicon ball, be placed in dry toluene, stirs
Under the conditions of amino silicane coupling agent is added dropwise, flow back under nitrogen protection, will amido modified silica gel material wash after be dried in vacuo
Night；
Corsslinking molecular is introduced into and is present on the amino in the silica gel material of surface modification: by the first step by step 2
Resulting amido modified silica gel material is placed in ultrasound in dry toluene, rapidly joins organic crosslinking agent molecule, nitrogen under condition of ice bath
It flows back under gas shielded；
Step 3, after washing under the intermediate product nitrogen protection that second step is reacted, the pyridine that bacitracin is added is molten
Liquid, stirred under nitrogen atmosphere reflux.
The reaction dosage mass ratio of silica gel material and the amino silicane coupling agent be 1/2~2, reflux temperature be 90~
125 DEG C, reflux duration 4~for 24 hours.
The reaction dosage mass ratio of amido modified silica gel material and the organic crosslinking agent molecule is 0.8~1.2, reflux
Temperature is 65~85 DEG C, and flow back 2~4h of duration.
The pyridine solution of the bacitracin is 0.2~0.8mol/L, and reflux temperature is 70~80 DEG C, reflux duration 12~
24h。
Compared with prior art, the invention has the benefit that the bacitracin primary colours of the method preparation by chemical bonding
Stationary phase is composed, is a kind of chromatographic stationary phases with hydrophilic nmature.The stationary phase preparation method is simple, and synthetic route is short, bonding
It is high-efficient.Technology is applied widely, all has good separation selectivity to most polar compounds, can be widely used for pole
Property sample separation.
Detailed description of the invention
Fig. 1 is the infrared spectrogram of bacitracin bonding type chromatograph packing material in embodiment 2；
Fig. 2 is bacitracin bonding front and back silica gel material pattern comparison diagram (SEM) in embodiment 2；
Fig. 3 is bacitracin bonding front and back silica gel material varying aperture comparison diagram in embodiment 2；
Fig. 4 is chromatogram of the Sebivo on bacitracin bonding type chromatographic stationary phases in example 4；
Fig. 5 is chromatogram of the vitamin B12 on bacitracin bonding type chromatographic stationary phases in example 5；
Fig. 6 is chromatogram of the vitamin B2 on bacitracin bonding type chromatographic stationary phases in example 6；
Fig. 7 is chromatogram of the vitamin B6 on bacitracin bonding type chromatographic stationary phases in example 7；
Fig. 8 is chromatogram of the Ofloxacin on bacitracin bonding type chromatographic stationary phases in example 8；
Fig. 9 is chromatogram of the Lafutidine on bacitracin bonding type chromatographic stationary phases in example 9.
Specific embodiment
The present invention is described in further detail for citing below.
The present embodiment is chemically bonded to by spacerarm with 3- aminopropyl-triethoxy using natural cyclic bacitracin as raw material
It is made on the silica-gel carrier of silane progress silanization.Present embodiment uses following technical scheme:
Example 1
(1) silanization of carrier silica gel
3g activated silica gel and 60mL dry toluene are added into two neck flask of 100mL, ultrasound makes silicon ball be uniformly dispersed, ice bath
Under the conditions of be added dropwise 2.5mL3- aminopropyl triethoxysilane while stirring, 90 DEG C of reflux for 24 hours, are cooled under the conditions of nitrogen protection
After room temperature, washed respectively 3 times with dry toluene and methanol, 40 DEG C are dried in vacuo to obtain 3- Aminopropyl silica gel；
(2) it is bonded the synthesis of bacitracin base chromatographic stationary phases
The 3- Aminopropyl silica gel of the above-mentioned drying of 2.5g is taken, 50mL dry toluene is added, ultrasound 5 minutes is fast under condition of ice bath
Speed be added 2.5mL hexamethylene diisocyanate, the lower 70 DEG C of back flow reaction 4h of nitrogen protection, after being cooled to room temperature remove solvent and
The anhydrous pyridine solution of 80mL bacitracin containing 0.8g, the lower 70 DEG C of back flow reactions of nitrogen protection is added in hexamethylene diisocyanate
It is washed after 20h with pyridine, methanol, 40 DEG C are dried in vacuo to obtain bacitracin bonding type chromatograph stationary-phase stuffing.
Example 2
(1) silanization of carrier silica gel
5g activated silica gel and 120mL dry toluene are added into two neck flask of 250mL, ultrasound makes silicon ball be uniformly dispersed, ice
2.5mL3- aminopropyl triethoxysilane is added dropwise under the conditions of bath while stirring, 125 DEG C of reflux 4h under the conditions of nitrogen protection are cooling
To room temperature, washed respectively 3 times with dry toluene and methanol, 40 DEG C are dried in vacuo to obtain 3- Aminopropyl silica gel；
(2) it is bonded the synthesis of bacitracin base chromatographic stationary phases
The 3- Aminopropyl silica gel of the above-mentioned drying of 2.5g is taken, 50mL dry toluene is added, ultrasound 5 minutes is fast under condition of ice bath
Speed be added 2.5mL hexamethylene diisocyanate, the lower 85 DEG C of back flow reaction 2h of nitrogen protection, after being cooled to room temperature remove solvent and
The anhydrous pyridine solution of 80mL bacitracin containing 0.8g, the lower 75 DEG C of back flow reactions of nitrogen protection is added in hexamethylene diisocyanate
It is washed after 12h with pyridine, methanol, 40 DEG C are dried in vacuo to obtain bacitracin bonding type chromatograph stationary-phase stuffing.
The chromatograph packing material elemental analysis result that the embodiment of the present invention 1,2 obtains see the table below
Fig. 1 is the infrared spectrogram of bacitracin bonding type chromatograph packing material in embodiment 2；
Fig. 2 is bacitracin bonding front and back silica gel material varying aperture comparison diagram in embodiment 2；
Fig. 3 is bacitracin bonding front and back silica gel material varying aperture comparison diagram in embodiment 2.
Embodiment 3
The fixed phase stuffing 2.0g that Example 2 obtains, homogenate method are filled in 100 × 4.6mm I.D. stainless steel column,
Dress column pressure is 60MPa.Gained is bacitracin bonding type chromatographic column.
Embodiment 4
Sebivo, the specific separation parameter of the Sebivo are analyzed using the obtained chromatography post separation of embodiment 3
It is as follows:
Mobile phase is acetonitrile: water (95: 5), flow velocity 1mL/min, Detection wavelength 267nm, and column temperature is 25 DEG C.
Fig. 4 is chromatogram of the Sebivo on bacitracin bonding type chromatographic stationary phases.
Embodiment 5
Vitamin B12 is analyzed using the obtained chromatography post separation of embodiment 3, the vitamin B12 specifically separates ginseng
Number is as follows:
Mobile phase is acetonitrile: water (80: 20), flow velocity 1mL/min, Detection wavelength 361nm, and column temperature is 25 DEG C.
Fig. 5 is chromatogram of the vitamin B12 on bacitracin bonding type chromatographic stationary phases.
Embodiment 6
Vitamin B2, the specific separation parameter of the vitamin B2 are analyzed using the obtained chromatography post separation of embodiment 3
It is as follows:
Mobile phase is acetonitrile: water (80: 20), flow velocity 1mL/min, Detection wavelength 444nm, and column temperature is 35 DEG C.
Fig. 6 is chromatogram of the vitamin B2 on bacitracin bonding type chromatographic stationary phases.
Embodiment 7
Vitamin B6, the specific separation parameter of the vitamin B6 are analyzed using the obtained chromatography post separation of embodiment 3
It is as follows；
Mobile phase is acetonitrile: water (95: 5), flow velocity 1mL/min, Detection wavelength 291nm, and column temperature is 25 DEG C.
Fig. 7 is chromatogram of the vitamin B6 on bacitracin bonding type chromatographic stationary phases.
Embodiment 8
Ofloxacin, the specific separation parameter of the Ofloxacin are analyzed using the obtained chromatography post separation of embodiment 3
It is as follows:
Mobile phase is acetonitrile: water (80: 20), flow velocity 1mL/min, Detection wavelength 294nm, and column temperature is 25 DEG C.
Fig. 8 is chromatogram of the Ofloxacin on bacitracin bonding type chromatographic stationary phases.
Embodiment 9
Lafutidine, the specific separation parameter of the Lafutidine are analyzed using the obtained chromatography post separation of embodiment 3
It is as follows:
Mobile phase is acetonitrile: water (80: 20), flow velocity 1mL/min, Detection wavelength 220nm, and column temperature is 25 DEG C.
Fig. 9 is chromatogram of the Lafutidine on bacitracin bonding type chromatographic stationary phases.
Although above in conjunction with attached drawing, invention has been described, it should be appreciated that the invention is not limited to above-mentioned
Specific embodiment, above-mentioned specific embodiment are only illustrative, rather than restrictive, and the technical staff of the industry should
Understand, without deviating from the spirit of the invention, the present invention can also make many changes and improvements, these belong to this hair
Within bright protection.The scope of the present invention is defined by the appended claims and its equivalents.
Claims (9)
1. a kind of chromatograph stationary-phase stuffing, it is characterised in that: be bonded the bacitracin containing amide groups, the stationary phase on silica gel material
Filler has hydrophilic nmature.
2. chromatograph stationary-phase stuffing according to claim 1, it is characterized in that the silica gel material is spherical porous silica gel,
The partial size of spherical porous chromatographic grade silica gel is 1~50 μm, and average pore size is
3. chromatograph stationary-phase stuffing according to claim 1, it is characterized in that the silica gel material used it is shown in following formula
Silane coupling agent surface treatment:
Wherein, R1~R3It respectively represents saturation or unsaturated alkyl with 1~20 carbon atom or there is 1~8 carbon atom simultaneously
There can be one or two carbon atom and can have the saturation or unsaturated alkyl of one or two or more a substituent groups；Y is
Containing amino, the alkyl with 1~10 carbon atom, alkoxy or azepine-silicyl；And the substituent group that the hydrocarbon can have is only
On the spot represent itrile group, hydroxyl, amino, pyridine or amide groups.
4. fixed phase stuffing according to any one of claims 1 to 3, it is characterized in that organic crosslinking agent molecule is in molecule
In with multiple isocyanate group compound.
5. the preparation method of fixed phase stuffing described in any one according to claim 1~4, which is characterized in that including following
Step:
Step 1, the processing of silica gel material surface amino groups silane coupling agent: taking activation silicon ball, be placed in dry toluene, stirring condition
Lower dropwise addition amino silicane coupling agent flows back under nitrogen protection, and silica gel material that will be amido modified is dried in vacuum overnight after washing；
Organic crosslinking agent molecule is introduced into and is present on the amino in the silica gel material of surface modification: by first by step 2
It walks resulting amido modified silica gel material and is placed in ultrasound in dry toluene, rapidly join organic crosslinking agent molecule under condition of ice bath,
It flows back under nitrogen protection；
The pyridine solution of bacitracin, nitrogen is added after washing under the intermediate product nitrogen protection for reacting second step in step 3
It is stirred at reflux under gas shielded.
6. the preparation method of fixed phase stuffing according to claim 5, it is characterised in that: silica gel material and ammonia in step 1
The reaction dosage mass ratio of base silane coupling agent is 1/2~2, and reflux temperature is 90~125 DEG C, reflux duration 4~for 24 hours.
7. the preparation method of fixed phase stuffing according to claim 5, it is characterised in that: amido modified silica gel in step 2
The reaction dosage mass ratio of material and organic crosslinking agent molecule is 0.8~1.2, and reflux temperature is 65~85 DEG C, reflux duration 2~
4h。
8. the preparation method of fixed phase stuffing according to claim 5, it is characterised in that: the pyridine of bacitracin in step 3
Solution is 2~10mg/mL, and reflux temperature is 70~80 DEG C, reflux duration 12~for 24 hours.
9. method system described in fixed phase stuffing described in Claims 1 to 4 any one or claim 5~8 any one
Application of the standby fixed phase stuffing as chromatographic column filler.
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| CN115814772B (en) * | 2022-10-19 | 2024-06-21 | 华东理工大学 | A bond and dipeptide silica stationary phase and its application in chromatographic separation of chitosan oligosaccharides |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103272573A (en) * | 2013-05-09 | 2013-09-04 | 中国药科大学 | Novel hybrid mesoporous silica gel chromatographic stationary phase and preparation method thereof |
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| CN103272573A (en) * | 2013-05-09 | 2013-09-04 | 中国药科大学 | Novel hybrid mesoporous silica gel chromatographic stationary phase and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| Binding of bacitracin to cells and protoplasts of Micrococcus lysodeikticus;DANIEL R. STORMI AND JACK L. STROMINGER;《THE JOURNAO OF BIOLOGICAL CHEMISTRY》;19730912;第249卷(第8期);全文 * |
| 环肽硅胶液相色谱固定相的制备及色谱行为研究;李媛媛等;《西北地区第七届色谱学术报告会甘肃省第十二届色谱年会论文集》;20120731;第91页 * |
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