CN106861662B - Amphoteric ion hydrophilic Interaction Chromatography stationary phase, the preparation method and applications that zwitterion is bonded respectively - Google Patents
Amphoteric ion hydrophilic Interaction Chromatography stationary phase, the preparation method and applications that zwitterion is bonded respectively Download PDFInfo
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- 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
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- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
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- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/32—Bonded phase chromatography
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Abstract
Amphoteric ion hydrophilic Interaction Chromatography stationary phase, the preparation method and applications that zwitterion is bonded respectively, belong to Stationary Phase of HPLC field, the amphoteric ion hydrophilic Interaction Chromatography stationary phase is reacted by " sulfydryl-double bond " click chemistry, and the silica ball surface that ionic liquid is bonded to the modification of 3- mercaptopropyi is prepared.The preparation method comprises the following steps: preparing the methylimidazole ionic liquid that end is acrylate structural first, and the ionic liquid that the zwitterion that end is acrylate structural combines must be arrived by ion exchange；By Silanization reaction in silica spheres surface grafting 3- mercaptopropyi group, then utilize the reaction of " sulfydryl-alkenyl " click chemistry that ionic liquid is bonded to the silicon ball surface for being modified with 3- mercaptopropyi.The hydrophilic Interaction Chromatography stationary phase, which shows different types of polarity and hydrophilic compounds, to be effectively maintained and separation selectivity, shows good application prospect.
Description
Technical field
The invention belongs to Stationary Phase of HPLC fields, and in particular to a kind of both sexes that zwitterion is grafted respectively from
Sub- bonded silica gel is as hydrophilic Interaction Chromatography stationary phase, preparation method and separation application.
Background technique
In recent years, hydrophilic Interaction Chromatography (HILIC) is more and more answered in terms of separating polar and hydrophily sample
With, obtained extensive concern, had become the research hotspot of chromatographic field at present, can be good at retain reverse-phase chromatography
(RPLC) do not retain or retain weak highly polar and hydroaropic substance in, while solving the molten of sample in normal-phase chromatography (NPLC)
Solution property problem and improve with mass spectrographic compatibility, show extraordinary application prospect.It is fixed for the application of HILIC
The exploitation of phase has a very big impact selectivity and separative efficiency, decides the application of HILIC to a certain extent.However,
Still have that hydrophily is insufficient, column effect is low, the service life is shorter and type is limited to polar compounds in terms of HILIC stationary phase at present
The problems such as covering of object is insufficient, therefore, the exploitation of novel HILIC stationary phase promote its hair for the coverage area of extension HILIC
Exhibition is of great significance, and has become the important research branch of chromatographic field now.HILIC stationary phase mainly includes direct at present
Use NPLC stationary phase (such as naked silica gel, amino, cyano and glycol-based modification material) and the special use developed in recent years
In the stationary phase of HILIC, some polarity and hydrophilic molecule are mainly bonded to matrix support material surface (usually silicon
Glue), such as common amide group, carbohydrate polyhydroxy molecule and amphoteric ion etc..Wherein, it is existed simultaneously in amphoteric ion molecule
Positive and negative charge center, have good hydrophily so that it is highly suitable as HILIC Bonded Phase, this kind of HILIC stationary phase mesh
The preceding good chromatographic performance of display, is widely used.Mainly had based on zwitterionic HILIC stationary phase based on sulfo group sweet tea
The amphoteric ion bonded silica gel material (ZIC-HILIC and ZIC-cHILIC) and some both sexes newly developed of dish alkali and phosphocholine
Ionic bonding stationary phase such as passes through the Click TE-Cys based on cysteine of " sulfydryl-alkenyl " click chemistry reaction preparation
Amphoteric ion HILIC stationary phase, and it is based on 3-P, P- diphenylphosphine-propyl sulfonic acid, lysine, glutathione and 1- ethylene
The amphoteric ion HILIC stationary phase of base -3- (4- sulfonate radical butane) imidazoles.In these amphoteric ion stationary phases, charge groups and
Distribution form has different, but positive and negative charge center passes through covalent bond and is connected in molecular structure, and entire molecule passes through
Certain mode is bonded to fixed phase surface, positive and negative although showing good HILIC reservation and separation to hydroaropic substance
Charge arrangement constraint mutually, is unable to free extension to interact with analyte.
For ionic liquid as stationary phase binding molecule, design is strong, and it is different types of can to design synthesis according to demand
The Bonded Phase met the requirements, in addition, the interaction of ionic liquid multiple solventization is conducive to the interaction with solute molecule, from
And provide good reservation and separation selectivity.Therefore, ionic liquid bonded stationary phase is greatly being developed nearly ten years,
It is mainly used for reverse phase and ion exchange mode, and also showed that preliminary potentiality in the field HILIC in recent years, that newly reports is novel
Surface bond ionic liquid stationary phase shows under HILIC mode and is effectively maintained and separates, including imidazoles amphoteric ion, glucose
Amine ionic liquid, double sun and three cation liquid surface are bonded HILIC stationary phase, and the designability of ionic liquid is but also just
Retain in the good structure HILIC of design hydrophilicity.Ionic liquid bonded silica stationary phase is by single yin at present
Ion or cation bonding introduce fixed phase surface, if it is bonding in solid that zwitterion is designed to active functional group
The structure of phase surface is determined, then obtained HILIC stationary phase is that zwitterion is bonded to silica gel table each by covalent bond respectively
The stationary phase in face is both the amphoteric ion stationary phase of surface bond ionic liquid stationary phase and new model, positive and negative charge distribution
It is not bound mutually, convenient for respectively preferably interacting with analyte, brings preferably reservation and unique separation selectivity,
And zwitterion proportion adjustment separates to improve.The present invention is based on this, send out exhibition zwitterion can distinguish covalence graft from
Sub- liquid, solid substrate is bonded to as new type amphoteric IONS OF H ILIC stationary phase, it should can be shown good
HILIC retention behavior and unique chromatographic performance.
Summary of the invention
In view of the problems of the existing technology, the present invention provides a kind of hydrophilic work of the amphoteric ion that zwitterion is bonded respectively
With chromatographic stationary phases, preparation method and applications.The zwitterion difference of the fixed phase surface of the amphoteric ion hydrophilic Interaction Chromatography
Filler surface is respectively grafted on by chemical bond, positive and negative charge distribution freely, can be acted on preferably with analyte.
The technical solution of the present invention is as follows:
The amphoteric ion hydrophilic Interaction Chromatography stationary phase that zwitterion is bonded respectively, the amphoteric ion hydrophilic Interaction Chromatography are solid
Fixed is mutually the material of the silica spheres surface bond ionic liquid A of 3- mercaptopropyi modification；Pass through " sulfydryl-double bond " clickization
Reaction is learned, the ionic liquid A silica ball surface for being bonded to the modification of 3- mercaptopropyi is prepared, binding molecule is end
It is the ionic liquid A of the zwitterion of acrylate structural.
The silica spheres of the 3- mercaptopropyi modification, pass through (3- mercaptopropyi) trimethoxy silane or (3- mercapto
Base propyl) triethoxysilane and silica spheres be heated to reflux under inert atmosphere in dry toluene it is obtained.Silica spheres
The bonding mole of the 3- mercaptopropyi group on surface is 2.0~4.0 μm of ol/m2。
The end ionic liquid A is the zwitterion of acrylate structural, be by counter ion be inorganic anion
It is prepared with two kinds of ionic liquids of inorganic cation by ion exchange；The surface bond of stationary phase intermediate ion liquid A
Mole is 1.5~3.0 μm of ol/m2；Its structural formula is as follows:
Wherein, the integer that n and m is 0~2；Anion part X-For SO3 2-、PO4 3-、PF6 -、BF4 -Or COO-One of；
Cationic portion Y+For imidazoles positive chargeQuaternary ammonium root cation, phosphonium salt cation or some other cation
Structure.
The preparation method of above-mentioned amphoteric ion hydrophilic Interaction Chromatography stationary phase, includes the following steps:
1) silica spheres of 3- mercaptopropyi modification are prepared
Silica spheres and (3- mercaptopropyi) trimethoxy silane or (3- mercaptopropyi) triethoxysilane are pressed into matter
Amount is than being that 1:1~2:1 is added in dry toluene, under inert gas shielding, in 105-115 DEG C of condition heating reflux reaction 18~25
Hour, obtain the silica spheres that surface bond has 3- mercaptopropyi.Wherein, the volume of silica spheres quality and dry toluene
Amount ratio is 1g:10~15mL.
2) surface bond for obtaining step 1) has the silica spheres of 3- mercaptopropyi to be scattered in dissolving ion liquid A
In methanol, initiator A IBN is added, after mixing evenly, under inert gas shielding, it is anti-to be heated to reflux in 50~70 DEG C of conditions
It answers 16~30 hours and obtains target stationary phase.
The molar ratio of acrylic double bond and 3- mercaptopropyi functional group in the ionic liquid A is 1.0~2.0:
1；The quality of the initiator be 3- mercaptopropyi silica spheres and ionic liquid A gross mass 0.5~2%.
Ionic liquid A's the preparation method comprises the following steps: preparation end is the methylimidazole ionic liquid of acrylate structural, and passes through
Ion exchange must arrive the ionic liquid A that the zwitterion that end is acrylate structural combines.
3) homogenate method is used, disperses the target fixed phase stuffing that step 2) obtains in methanol and homogenate is made, wherein
The ratio of target stationary phase quality and methanol volumetric usage is 1.0g:10~15mL；Again using methanol as displacement fluid, 50~
Under the pressure of 65MPa, it is solid that filling obtains the amphoteric ion hydrophilic Interaction Chromatography that zwitterion is bonded respectively into stainless-steel tubing pillar
Fixed column, the amphoteric ion hydrophilic Interaction Chromatography stationary phase that chromatography fixed column the interior of the body belonging to YIN cation is bonded respectively.
Above-mentioned amphoteric ion hydrophilic Interaction Chromatography stationary phase is different types of for separating under hydrophilic Interaction Chromatography mode
Polarity and hydroaropic substance can selectively pass through the proportion adjustment of change zwitterion.The polarity and hydroaropic substance
For the both sexes substance such as nucleosides and base, Organic Acid and Base drug and amino acid.
Beneficial effects of the present invention are that amphoteric ion HILIC stationary phase configuration and charge arrangement provided by the invention is novel,
Positive and negative charge structure is freely and mutually unaffected, the ratio of positive and negative charge can be also adjusted as needed, to different types of pole
Property and hydroaropic substance separation, display is effective retains and good separation selectivity, has certain application prospect.
Detailed description of the invention
The amphoteric ion stationary phase that Fig. 1 is bonded respectively for zwitterion prepares schematic diagram；
Fig. 2 is separation chromatogram of 17 kinds of mixture of nucleosides on prepared amphoteric ion column of the present invention；Wherein, chromatography
Peak: 1.5 '--5 '-methylthioadenosines of deoxidation, 2. thymidines, 3.3- methyluridine, 4.N6- methyladenosine, 5.5- methyl urine
Glycosides, 6. uridines, 7. adenosines, 8.5- methylcystein, 9.1- methylguanosine, 10. inosines, 11. pseudouridines, 12.2 '-deoxidation birds
Glycosides, 13. cytidines, 14. guanosines, 15.1- methyladenosine, 16. xanthosines, 17.7- methylguanosine；Separation condition is mobile phase 95%
ACN(10mM NH4FA)/H2O(10mM NH4FA)=90/10 (v/v), isocratic elution；DAD:254nm；Flow velocity: 0.4mL/min；
Column temperature: 30 DEG C；
Fig. 3 is the separation chromatogram of 11 kinds of bases；Wherein, chromatographic peak: 1. thymidines, 2. uracils, 3.1- methyl yellow
Purine, 4.N4Acetylcytosine, 5.1- methyl guanine, 6. adenines, 7. xanthine, 8. hypoxanthine, 9.7- methyl bird are fast
Purine, 10. cytimidines, 11. guanines；Separation condition: mobile phase 95%ACN (10mM NH4FA)/H2O(10mM NH4FA)=90/
10 (v/v), isocratic elution；DAD:254nm；Flow velocity: 0.4mL/min；Column temperature: 30 DEG C
Fig. 4 is the separation chromatogram of 12 kinds of mixture of ribonucleotides；Wherein, chromatographic peak: 1.cTMP, 2.3':5 '-cAMP,
3.2 ': 3 '-cAMP, 4.cIMP, 5.cGMP, 6.cCMP；7.TMP 8.UMP, 9.AMP, 10.IMP, 11.CMP, 12.GMP；Separation
Condition: mobile phase A is mutually H2O(10mM NH4FA), B phase is ACN/H2O (95/5, v/v, 10mM NH4FA), gradient elution with
20%A originates and keeps 5min, and 40%A is linearly increasing in 5-10min and is kept, DAD 254nm；Flow velocity 0.4mL/min, column
Temperature: 30 DEG C；
Fig. 5 (a) is the separation chromatogram of 6 kinds of alkaline matters；Wherein, it chromatographic peak: draws in 1.Diphenhydramine benzene sea
It is bright；2.Nortriptyline nortriptyline；3.Benzyltrimethylammonium benzyl trimethylammonium；
4.trimethylphenyl；5.procainamide；6.Benzylamine benzylamine；
Fig. 5 (b) is the separation chromatogram of 8 kinds of acidic materials；Wherein, chromatographic peak: 1. phenol；2.3,5- dinitrobenzene first
Acid；3. P-methoxybenzoic acid；4. paranitrobenzoic acid；5.3- chlorobenzoic acid；6. benzoic acid；7. P-hydroxybenzoic acid；Between 8.
Hydroxybenzoic acid separation condition: separation condition: mobile phase 95%ACN (10mM NH4FA)/H2O(10mM NH4FA)=90/10
(v/v), isocratic elution；DAD:254nm；Flow velocity: 0.4mL/min；Column temperature: 30 DEG C；
Fig. 6 is the separation chromatogram of 7 kinds of amphiprotic substances；Wherein, chromatographic peak: 1. p-aminobenzoic acid；2. hippuric acid；3. cigarette
Acid；4. orotic acid；5.phe；6.try；7.tyr；Separation condition: mobile phase 95%ACN (10mM NH4FA)/H2O(10mM
NH4FA)=85/15 (v/v), isocratic elution；DAD:254nm；Flow velocity: 0.4mL/min；Column temperature: 30 DEG C.
Specific embodiment
The present invention is further illustrated below by example, and example is only limitted to illustrate the present invention in order to understand, rather than to this
The restriction of invention.
The preparation for the ionic liquid that zwitterion can be bonded respectively
The preparation step for the amphoteric ion stationary phase that zwitterion is bonded respectively is as shown in Figure 1.By 1.23g 2- bromoethyl
Acrylate is dissolved in a small amount of ethyl acetate in, 3.0g 1- methylimidazole is added while stirring, under protection of argon gas reaction solution
It is protected from light about 24 hours, causes stirring motionless until reactant generates.It stands and removes upper layer solvent, sticky product acetic acid second
Ester washs 4-5 and removes unreacted raw material, and 60 DEG C of vacuum drying obtain product 1.Obtained product 1 and 3- sulfopropyl acrylic acid
Salt sylvite obtains product 2 by ion exchange, and product 2 is then bonded to silica ball surface and obtains target stationary phase.
The product 1 of synthesis and 3- sulfopropyl acrylates sylvite are subjected to ion exchange, prepares in zwitterion and contains
The product 2 of reactive active group, specific step is as follows.The product 1 of 1.4957g is dissolved in 15mL deionized water, is stirred
The lower 3- sulfopropyl acrylates sylvite 1.3332g for being added and being dissolved in 15mL deionized water is mixed, lower ion exchange is sufficiently stirred
Reaction carries out about 30 hours.The direct vacuum rotary steam of reaction solution is gone out moisture, and obtained product 2 is dried in vacuo in 60 DEG C, generation
NaBr salt does not remove, is gone out in subsequent the step of product 2 is bonded to Silica Surface by washing and centrifugation.
The preparation for the amphoteric ion stationary phase that zwitterion is bonded respectively
Firstly, by Silanization reaction in silica spheres surface grafting active function groups 3- mercaptopropyi, by 6.6g bis-
Silicon oxide ball (5 μm of partial size, aperture 10nm, specific surface area 310m2g-1) be dispersed in 72mL dry toluene, it stirs evenly, is added
4.0mL (3- mercaptopropyi) trimethoxy silane, is heated to reflux 24 hours under protection of argon gas, and centrifugation is washed 6 times with methanol,
Obtain the silica spheres of 3- mercaptopropyi modification, 60 DEG C of dried for standby of vacuum.
3- mercaptopropyi is bonded to secondly, the product 2 that embodiment obtains is reacted by sulfydryl with the click chemistry of double bond
The silicon ball that 3.24g 3- mercaptopropyi is modified is dispersed the 55mL methanol dissolved with product 2 by the silica ball surface of modification
In, be dispersed with stirring it is uniformly mixed, be added 0.08g be dissolved in the initiator A IBN in 10mL methanol, be heated under protection of argon gas
60 DEG C back flow reaction 26 hours, reaction solution centrifugation after, successively washed with methanol, water, methanol, obtain target stationary phase, vacuum 60
DEG C dry column to be installed.
Finally, the amphoteric ion fixed phase stuffing that obtained zwitterion is bonded respectively is packed into 3.0mm × 15cm's
Liquid-phase chromatographic column, using homogenate method, using 50mL methanol as displacement fluid, by homogenate (target stationary phase under the pressure of 60MPa
1.2g is dispersed in 12mL methanol) it fills into stainless-steel tubing pillar.
The evaluation for the amphoteric ion stationary phase that zwitterion is bonded respectively
Elemental analysis surface bond amount, result C%14.94, N%1.65, S% are carried out to gained stationary phase
The silica spheres elemental analysis result of 4.27,3- mercaptopropyis is C%3.93, S%2.64, is calculated with N and S constituent content,
The zwitterion bonded amount of stationary phase is suitable, about 2.05~2.30 μm of ol/m2。
Prepared amphoteric ion chromatographic column and HILIC retention property and separation selectivity are evaluated, divided first
It is as shown in Figures 2 and 3 respectively the separation to mixture of nucleosides and base mixture from typical hydrophilic and polar compound
Chromatogram.The results show that the stationary phase of preparation shows typical HILIC retention behavior, have very to Exemplary hydrophilic compound
Good separation selectivity.Later, using different types of hydrophilic and polar compound to the chromatographic performance of amphoteric ion stationary phase
It is further characterized, Fig. 4, Fig. 5 (a), (b) and Fig. 6 are respectively nucleotide, alkali compounds and acid compound and two
The separating resulting of property substance, it can be seen that prepared chromatographic column all has different types of polarity and hydrophilic compounds
Good reservation and separation selectivity have certain application potential as novel HILIC stationary phase.
Claims (8)
1. a kind of amphoteric ion hydrophilic Interaction Chromatography stationary phase that zwitterion is bonded respectively, which is characterized in that the both sexes
Ionic hydrophilic action chromatography stationary phase is the material of the silica spheres surface bond ionic liquid A of 3- mercaptopropyi modification；It is logical
The reaction of " sulfydryl-double bond " click chemistry is crossed, is prepared by the ionic liquid A silica ball surface for being bonded to the modification of 3- mercaptopropyi
It obtains；Binding molecule be end be acrylate structural zwitterion ionic liquid A；
The silica spheres of the 3- mercaptopropyi modification, pass through (3- mercaptopropyi) trimethoxy silane or (3- sulfydryl third
Base) triethoxysilane and silica spheres be heated to reflux under inert atmosphere in dry toluene it is obtained；
The ionic liquid A passes through ion by counter ion for two kinds of ionic liquids of inorganic anion and inorganic cation and hands over
It changes and is prepared；Its structural formula is as follows:
Wherein, the integer that n and m is 0~2；Anion part X-For SO3 2-、PO4 3-、PF6 -、BF4 -Or COO-One of；Sun from
Subdivision Y+For imidazoles positive chargeQuaternary ammonium root cation, phosphonium salt cation.
2. amphoteric ion hydrophilic Interaction Chromatography stationary phase according to claim 1, which is characterized in that the silica
The bonding mole of the 3- mercaptopropyi group of ball surface is 2.0~4.0 μm of ol/m2。
3. amphoteric ion hydrophilic Interaction Chromatography stationary phase according to claim 1 or 2, which is characterized in that the fixation
The surface bond mole of phase intermediate ion liquid A is 1.5~3.0 μm of ol/m2。
4. the preparation method of amphoteric ion hydrophilic Interaction Chromatography stationary phase, feature described in the claims 1 or 2 or 3 exist
In following steps:
1) silica spheres of 3- mercaptopropyi modification are prepared
By silica spheres and (3- mercaptopropyi) trimethoxy silane or (3- mercaptopropyi), triethoxysilane is in mass ratio
It is added in dry toluene for 1:1~2:1, it is small in 105-115 DEG C of condition heating reflux reaction 18~25 under inert gas shielding
When, obtain the silica spheres that surface bond has 3- mercaptopropyi；
2) methanol that the surface bond for obtaining step 1) has the silica spheres of 3- mercaptopropyi to be scattered in dissolving ion liquid A
In, initiator A IBN is added, after mixing evenly, under inert gas shielding, is heated to back flow reaction 16 in 50~70 DEG C of conditions
Obtain target stationary phase within~30 hours；
The molar ratio of acrylic double bond and 3- mercaptopropyi functional group in the ionic liquid A is 1.0~2.0:1；Institute
The quality for the initiator stated be 3- mercaptopropyi silica spheres and ionic liquid A gross mass 0.5~2%；
3) homogenate method is used, disperses the target fixed phase stuffing that step 2) obtains in methanol and homogenate is made, wherein target
The ratio of stationary phase quality and methanol volumetric usage is 1.0g:10~15mL；Again using methanol as displacement fluid, in certain pressure
Under, filling obtains the amphoteric ion hydrophilic Interaction Chromatography fixed column that zwitterion is bonded respectively into stainless-steel tubing pillar.
5. the preparation method of amphoteric ion hydrophilic Interaction Chromatography stationary phase according to claim 4, which is characterized in that step
1) the volumetric usage ratio of silica spheres quality and dry toluene described in is 1g:10~15mL.
6. the preparation method of amphoteric ion hydrophilic Interaction Chromatography stationary phase according to claim 4 or 5, which is characterized in that
Pressure described in step 3) is 50~65MPa.
7. the application of amphoteric ion hydrophilic Interaction Chromatography stationary phase described in the claims 1 or 2 or 3, which is characterized in that institute
The amphoteric ion hydrophilic Interaction Chromatography stationary phase stated is under hydrophilic Interaction Chromatography mode for separating different types of polarity and parent
Aqueous substance can selectively pass through the proportion adjustment of change zwitterion.
8. the application of amphoteric ion hydrophilic Interaction Chromatography stationary phase according to claim 7, which is characterized in that the pole
Property and hydroaropic substance be nucleosides and base, Organic Acid and Base drug and amino acid both sexes substance.
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