CN1994557A - Teicoplanin p-chlorophenyl isocyanate chiral stationary phase filling and method for preparing same - Google Patents
Teicoplanin p-chlorophenyl isocyanate chiral stationary phase filling and method for preparing same Download PDFInfo
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- CN1994557A CN1994557A CN 200610155012 CN200610155012A CN1994557A CN 1994557 A CN1994557 A CN 1994557A CN 200610155012 CN200610155012 CN 200610155012 CN 200610155012 A CN200610155012 A CN 200610155012A CN 1994557 A CN1994557 A CN 1994557A
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Abstract
The invention relates to a carbanilate group carbanilate group chirality fixed phase stuff and relative production, wherein it uses silica gel as carrier; the carrier and 3-propyl triethoxysilicane to process silanization reaction; activates the carrier and distant arm; bonds silica carrier and peptide macrocyclic antibiotics, processes derivation with carbanilate group. The inventive fixed phase stuff has high chirality recognize ability and high stability to be used in any spectrum conditions. The invention can separate glutacid in reverse flow phase, to separate the salbutamolum in polar flow phase.
Description
Technical field
The present invention relates to a kind of teicoplanin rubigan isocyanate chiral stationary phase filling and preparation method thereof, belongs to the analytical chemistry field.
Background technology
Chirality is one of the mankind's natural essential attribute of depending on for existence, and large biological molecule such as protein, polysaccharide, nucleic acid etc. have chirality entirely.Have optically active chiral material and extensively be formed in the bodies of aminal and plant, the solid of this biological stereoselectivity and optical rotatory substance is synthetic, is the distinctive instinct of biosystem.Two of enantiomter chipal compounds each other, in biologically active, pharmacological kinetics, often there is bigger difference the potential aspects such as toxic and side effect of medicine, the Western medicine of Chu Shouing has and contains chiral centre about half in the market, this wherein has only about half of again is to sell with the form of racemic modification, U.S. for this reason, the European Community and Japan, state administration of health departments such as Canada have proposed very strict requirement to new racemic medicine, requirement has clear and definite explanation to the metabolism and the medicine dynamics of its enantiomer, stipulate that every from now on development has the medicine of asymmetric center, must provide the chiral resolution result.
Solve the spatial chemistry problem with liquid chromatogram, the separating optical isomeric body is owing to having fast, simply, advantage is subjected to extensive attention efficiently.Development with chiral stationary phase (CSP) of dissimilar chiral centres or chiral Recognition ability is the field, forward position of chiral chromatogram development, also is the key and the core of chiral chromatogram development.The development of CSP starts from the seventies later stage, undergoes an unusual development rapidly.A large amount of various types of CSP (as Pirkle type CSP, protein type CSP, cyclodextrin type CSP, cellulose and glycan CSP, chiral crown ether and charge transfer type CSP etc.) succeed in developing in succession, and the CSP of part type is as commodity selling.
Since Armstrong in 1994 etc. are applied to the high performance liquid chromatography chiral stationary phase with glycopeptide antibiotics as chiral selector first, because the antibiotic enantio-selectivity height of this class, has chiral Recognition ability more widely, be referred to as the chiral selector of a new generation, become fixedly phase of the most potential at present class novel chiral.
Teicoplanin is the big cyclohexanol peptide antibiotics that is produced by Actinoplanes teichomyceticus bacterium, and it is used to treat the severe infections that is caused by grampostive bacteria.Verified now, five major ingredients in the teicoplanin, their difference each other just is the length difference [Ilaria D ' Acquarica of the alkyl chain of ining succession on the N-gucosamine, Francesco Gasparrini, Domenico Misiti, Claudio Villani, Angelo Carotti, Saverio Cellamare, Sandra Muck.Direct chromatographicresolution of carnitine and O-acylcarnitine enantiomers on a teicoplanin-bondedchiral stationary phase.Journal of Chromatography A, 857 (1999) 145-155].The rubigan isocyanate derivates of teicoplanin chiral stationary phase is used for chromatographic isolation as chiral selector, does not still have report at present both at home and abroad.
Summary of the invention
The purpose of this invention is to provide a kind of teicoplanin rubigan isocyanate chiral stationary phase filling and preparation method thereof.
It is that glycopeptide class macrocyclic antibiotic is chemically bonded on the silica-gel carrier, carries out the chiral chromatographic fixed phase stuffing that derivative reaction is made with the rubigan isocyanates again.
Described glycopeptide class macrocyclic antibiotic is the rubigan isocyanate derivates of teicoplanin and teicoplanin.Silica gel is chromatographic grade spherical silica gel or chromatographic grade amorphous silica gel.
The used spacerarm of chemical bonding is meant the 3-aminopropyl triethoxysilane, 1, and 6-vulcabond n-hexane or 1, the silylating reagent that 3-vulcabond benzene chemical bonding is used, the step of method is as follows:
1, the silanization of carrier silica gel
Silica-gel carrier is with 3～5mol L
-14～6 hours after washings of hydrochloric acid reflux are to neutral, and vacuum drying is made solvent with dry toluene, adds the 3-aminopropyl triethoxysilane, and back flow reaction 8～10 hours is cooled to room temperature and filters, and uses toluene, methanol wash successively, and vacuum drying gets 3-aminopropyl silica gel;
2, fixing phase synthetic of bonded chiral
Get the 3-aminopropyl silica gel of the above-mentioned drying of 3 grams; add dry toluene; under ice bath and nitrogen protection, drip 1 of 2～4ml; 6-vulcabond n-hexane or 1; 3-vulcabond benzene; mixture is heated to 65-75 ℃ of reaction 2～3 hours; be cooled to remove after the room temperature and desolvate and 1; 6-vulcabond n-hexane or 1; 3-vulcabond benzene adds 100ml and contains 1g teicoplanin anhydrous pyridine solution, and 65～75 ℃ of stirring reactions are 10～12 hours under the nitrogen protection; filter; use pyridine; water; methyl alcohol; acetonitrile; washed with dichloromethane, behind the drying under reduced pressure with the rubigan isocyanates in anhydrous pyridine solution 110～120 ℃ the reaction 2～3 hours, after the filtration; use pyridine successively; water; methyl alcohol; acetone; the washed with dichloromethane drying gets teicoplanin rubigan isocyanate chiral chromatograph stationary-phase stuffing.
Described glycopeptide class macrocyclic antibiotic is the rubigan isocyanate derivates of teicoplanin and teicoplanin.Silica gel is chromatographic grade spherical silica gel or chromatographic grade amorphous silica gel.
The teicoplanin rubigan isocyanate chiral of the method preparation of the present invention by chemical bonding is phase fixedly, has separated glutamic acid in anti-phase system, at the mobile medicine such as salbutamol that separated in mutually of polarity.
The preparation method is simple for this chiral stationary phase, and can use under positive, anti-phase and polarity organic facies isochromatic spectrum pattern, and the chiral Recognition ability of chromatographic column is unaffected.In anti-phase system, separate glutamic acid, in polarity flows mutually, separated salbutamol, can satisfy the needs of the daily Pharmaceutical Analysis and quality of production control.
Description of drawings
Fig. 1 is that glutamic acid (Glutamic acid) is at the fixing fractionation chromatogram of going up mutually of teicoplanin rubigan isocyanate chiral;
Phase flows: ethanol/water=60/40 (v/v); Flow velocity is: 0.5ml/min; Column temperature: 25 ℃; Detect wavelength: 207nm.
Fig. 2 is that salbutamol (Salbutamol) beta-blocker is at the fixing fractionation chromatogram of going up mutually of teicoplanin rubigan isocyanate chiral;
Phase flows: methyl alcohol/glacial acetic acid/triethylamine=100/0.1/0.1 (v/v/v); Flow velocity is: 1.0ml/min; Column temperature: 25 ℃; Detect wavelength: 225nm.
The specific embodiment
Teicoplanin rubigan isocyanate chiral chromatograph stationary-phase stuffing can separate the chiral drug or the amino acid of multiple structure type.Simultaneously, prepared fixing has good stability mutually, is suitable as efficient liquid phase chromatographic stuffing.
Teicoplanin rubigan isocyanate chiral chromatograph stationary-phase stuffing is that glycopeptide class macrocyclic antibiotic-teicoplanin is chemically bonded on the silica-gel carrier, carries out derivative reaction with the rubigan isocyanates again and makes.
Below by example the present invention is specifically addressed, but is not limited thereto.
The present invention is a raw material with glycopeptide class macrocyclic antibiotic-teicoplanin,, carries out derivative reaction with the benzene isocyanates again and makes to carrying out on the silica-gel carrier of silanization with 3-(aminopropyl)-triethoxysilane by the spacerarm chemical bonding.
1, the silanization of carrier silica gel
Silica-gel carrier is with 3～5mol L
-14～6 hours after washings of hydrochloric acid reflux are to neutral, and vacuum drying is made solvent with dry toluene, adds the 3-aminopropyl triethoxysilane, and back flow reaction 8～10 hours is cooled to room temperature and filters, and uses toluene, methanol wash successively, and vacuum drying gets 3-aminopropyl silica gel;
2, fixing phase synthetic of bonded chiral
Get the 3-aminopropyl silica gel of the above-mentioned drying of 3 grams; add dry toluene; under ice bath and nitrogen protection, drip 1 of 2～4ml; 6-vulcabond n-hexane or 1; 3-vulcabond benzene; mixture is heated to 65-75 ℃ of reaction 2～3 hours; be cooled to remove after the room temperature and desolvate and 1; 6-vulcabond n-hexane or 1; 3-vulcabond benzene adds 100ml and contains 1g teicoplanin anhydrous pyridine solution, and 65～75 ℃ of stirring reactions are 10～12 hours under the nitrogen protection; filter; use pyridine; water; methyl alcohol; acetonitrile; washed with dichloromethane, behind the drying under reduced pressure with the rubigan isocyanates in anhydrous pyridine solution 110～120 ℃ the reaction 2～3 hours, after the filtration; use pyridine successively; water; methyl alcohol; acetone; the washed with dichloromethane drying gets teicoplanin rubigan isocyanate chiral chromatograph stationary-phase stuffing.
3, the separation of glutamic acid enantiomer in anti-phase system
Mobile phase composition is ethanol/water=60/40 (v/v), chiral separation factor-alpha=1.69, and separating degree Rs=1.59, chromatogram is seen Fig. 1.
4, the separation of salbutamol enantiomer in the polarity organic facies
Mobile phase composition be methyl alcohol/glacial acetic acid/triethylamine (100/0.1/0.1, v/v/v), chiral separation factor-alpha=1.24, separating degree Rs=1.87, the separate colors spectrogram under this condition is seen Fig. 2.
Embodiment 1
1) silanization of carrier silica gel
Take by weighing 10 gram Kromasil spherical silica gel carriers (particle diameter 5 μ m, aperture 10nm) and use 3mol L
-14 hours after washings of hydrochloric acid reflux are to neutral, and vacuum drying is made solvent with dry toluene, adds the 3-aminopropyl triethoxysilane of 10ml, and back flow reaction 8 hours is cooled to room temperature and filters, and with toluene and methanol wash, vacuum drying gets 3-aminopropyl silica gel;
2) fixing phase synthetic of bonded chiral
Get the 3-aminopropyl silica gel of the above-mentioned drying of 3 grams; add in the dry toluene; under ice bath and nitrogen protection, drip 1 of 2ml; 6-vulcabond n-hexane; mixture is heated to 65 ℃ of reactions 2 hours; be cooled to remove after the room temperature and desolvate and 1; 6-vulcabond n-hexane; add 100ml and contain 1g teicoplanin anhydrous pyridine solution; the following 65 ℃ of stirring reactions of nitrogen protection 10 hours; filter; use pyridine; water; methyl alcohol; acetonitrile; washed with dichloromethane, behind the drying under reduced pressure with phenyl isocyanate in anhydrous pyridine solution 110 ℃ the reaction 2 hours, after the filtration; use pyridine; water; methyl alcohol; acetone; the washed with dichloromethane drying gets teicoplanin rubigan isocyanate chiral chromatograph stationary-phase stuffing.
Embodiment 2
1) silanization of carrier silica gel
Take by weighing 10 gram Lichrosorb amorphous silica gel carriers (particle diameter 5 μ m, aperture 10nm) and use 5mol L
-16 hours after washings of hydrochloric acid reflux are to neutral, and vacuum drying is made solvent with dry toluene, adds the 3-aminopropyl triethoxysilane, and back flow reaction 10 hours is cooled to room temperature and filters, and with toluene and methanol wash, vacuum drying gets 3-aminopropyl silica gel;
2) fixing phase synthetic of bonded chiral
Get the 3-aminopropyl silica gel of the above-mentioned drying of 3 grams; add in the dry toluene; under ice bath and nitrogen protection, drip 1 of 3ml; 6-vulcabond n-hexane; mixture is heated to 70 ℃ of reactions 3 hours; be cooled to remove after the room temperature and desolvate and 1; 6-vulcabond n-hexane; add 100ml and contain 2g teicoplanin anhydrous pyridine solution; the following 70 ℃ of stirring reactions of nitrogen protection 10 hours; filter; use pyridine; water; methyl alcohol; acetonitrile; washed with dichloromethane, behind the drying under reduced pressure with phenyl isocyanate in anhydrous pyridine solution 110 ℃ the reaction 3 hours, after the filtration; use pyridine; water; methyl alcohol; acetone; the washed with dichloromethane drying gets teicoplanin rubigan isocyanate chiral chromatograph stationary-phase stuffing.
Embodiment 3
1) silanization of carrier silica gel
Take by weighing 10 gram Lichrospher spherical silica gel carriers (particle diameter 5 μ m, aperture 10nm) and use 5mol L
-14 hours after washings of hydrochloric acid reflux are to neutral, and vacuum drying is made solvent with dry toluene, adds the 3-aminopropyl triethoxysilane, and back flow reaction 8 hours is cooled to room temperature and filters, and with toluene and methanol wash, vacuum drying gets 3-aminopropyl silica gel;
2) fixing phase synthetic of bonded chiral
Get the 3-aminopropyl silica gel of the above-mentioned drying of 3 grams; add in the dry toluene; under ice bath and nitrogen protection, drip 1 of 4ml; 6-vulcabond n-hexane; mixture is heated to 75 ℃ of reactions 3 hours; be cooled to remove after the room temperature and desolvate and 1; 6-vulcabond n-hexane; add 100ml and contain 2g teicoplanin anhydrous pyridine solution; the following 75 ℃ of stirring reactions of nitrogen protection 12 hours; filter; use pyridine; water; methyl alcohol; acetonitrile; washed with dichloromethane, behind the drying under reduced pressure with phenyl isocyanate in anhydrous pyridine solution 120 ℃ the reaction 3 hours, after the filtration; use pyridine; water; methyl alcohol; acetone; the washed with dichloromethane drying gets teicoplanin rubigan isocyanate chiral chromatograph stationary-phase stuffing.
Embodiment 4
1) silanization of carrier silica gel
Take by weighing 10 gram Kromasil spherical silica gel carriers (particle diameter 5 μ m, aperture 20nm) and use 5mol L
-14 hours after washings of hydrochloric acid reflux are to neutral, and vacuum drying is made solvent with dry toluene, adds the 3-aminopropyl triethoxysilane, and back flow reaction 8 hours is cooled to room temperature and filters, and with toluene and methanol wash, vacuum drying gets 3-aminopropyl silica gel;
2) fixing phase synthetic of bonded chiral
Get the 3-aminopropyl silica gel of the above-mentioned drying of 3 grams; add in the dry toluene; under ice bath and nitrogen protection, drip 1 of 4ml; 6-vulcabond n-hexane; mixture is heated to 75 ℃ of reactions 3 hours; be cooled to and desolventize after the room temperature and 1; 6-vulcabond n-hexane; add 100ml and contain 2g teicoplanin anhydrous pyridine solution; the following 75 ℃ of stirring reactions of nitrogen protection 12 hours; filter; use pyridine; water; methyl alcohol; acetonitrile; washed with dichloromethane, behind the drying under reduced pressure with phenyl isocyanate in anhydrous pyridine solution 120 ℃ the reaction 3 hours, after the filtration; use pyridine; water; methyl alcohol; acetone; the washed with dichloromethane drying gets teicoplanin rubigan isocyanate chiral chromatograph stationary-phase stuffing.
Embodiment 5
Bonded chiral is synthesizing of phase fixedly
Take by weighing dry Kromasil-NH2 spherical silica gel carrier (the particle diameter 5 μ m of 3 grams; aperture 10nm); add in the dry toluene; under ice bath and nitrogen protection, drip 1 of 4ml; 6-vulcabond n-hexane; mixture is heated to 75 ℃ of reactions 3 hours; be cooled to remove after the room temperature and desolvate and 1; 6-vulcabond n-hexane; add 100ml and contain 2g teicoplanin anhydrous pyridine solution; the following 75 ℃ of stirring reactions of nitrogen protection 12 hours filter, and use pyridine; water; methyl alcohol; acetonitrile; washed with dichloromethane; behind the drying under reduced pressure with phenyl isocyanate in anhydrous pyridine solution 120 ℃ the reaction 3 hours; after the filtration, use pyridine; water; methyl alcohol; acetone; the washed with dichloromethane drying gets teicoplanin rubigan isocyanate chiral chromatograph stationary-phase stuffing.
Embodiment 6
1) silanization of carrier silica gel
Take by weighing 10 Crane institute spherical silica gel carriers (particle diameter 5 μ m, aperture 9nm) and use 5mol L
-14 hours after washings of hydrochloric acid reflux are to neutral, and vacuum drying is made solvent with dry toluene, adds the 3-aminopropyl triethoxysilane, and back flow reaction 8 hours is cooled to room temperature and filters, and with toluene and methanol wash, vacuum drying gets 3-aminopropyl silica gel;
2) fixing phase synthetic of bonded chiral
Get the 3-aminopropyl silica gel of the above-mentioned drying of 3 grams; add in the dry toluene; under ice bath and nitrogen protection, drip 1 of 4ml; 6-vulcabond n-hexane; mixture is heated to 75 ℃ of reactions 3 hours; be cooled to remove after the room temperature and desolvate and 1; 6-vulcabond n-hexane; add 100ml and contain 2g teicoplanin anhydrous pyridine solution; the following 75 ℃ of stirring reactions of nitrogen protection 12 hours; filter; use pyridine; water; methyl alcohol; acetonitrile; washed with dichloromethane, behind the drying under reduced pressure with phenyl isocyanate in anhydrous pyridine solution 120 ℃ the reaction 3 hours, after the filtration; use pyridine; water; methyl alcohol; acetone; the washed with dichloromethane drying gets teicoplanin rubigan isocyanate chiral chromatograph stationary-phase stuffing.
Claims (6)
1, a kind of teicoplanin rubigan isocyanate chiral chromatograph stationary-phase stuffing, it is characterized in that: it is that glycopeptide class macrocyclic antibiotic is chemically bonded on the silica-gel carrier, carries out the chiral chromatographic fixed phase stuffing that derivative reaction is made with the rubigan isocyanates again.
2, according to the described teicoplanin rubigan of claim 1 isocyanate chiral stationary phase filling, it is characterized in that: described glycopeptide class macrocyclic antibiotic is the rubigan isocyanate derivates of teicoplanin and teicoplanin.
3, teicoplanin rubigan isocyanate chiral chromatograph stationary-phase stuffing according to claim 1, it is characterized in that: described silica gel is chromatographic grade spherical silica gel or chromatographic grade amorphous silica gel.
4, a kind of preparation method of teicoplanin rubigan isocyanate chiral chromatograph stationary-phase stuffing, it is characterized in that: the used spacerarm of described chemical bonding is meant the 3-aminopropyl triethoxysilane, 1,6-vulcabond n-hexane or 1, the silylating reagent that 3-vulcabond benzene chemical bonding is used, the step of method is as follows:
1) silanization of carrier silica gel
Silica-gel carrier is with 3～5mol L
-14～6 hours after washings of hydrochloric acid reflux are to neutral, and vacuum drying is made solvent with dry toluene, adds the 3-aminopropyl triethoxysilane, and back flow reaction 8～10 hours is cooled to room temperature and filters, and uses toluene, methanol wash successively, and vacuum drying gets 3-aminopropyl silica gel;
2) fixing phase synthetic of bonded chiral
Get the 3-aminopropyl silica gel of the above-mentioned drying of 3 grams; add dry toluene; under ice bath and nitrogen protection, drip 1 of 2～4ml; 6-vulcabond n-hexane or 1; 3-vulcabond benzene; mixture is heated to 65-75 ℃ of reaction 2～3 hours; be cooled to remove after the room temperature and desolvate and 1; 6-vulcabond n-hexane or 1; 3-vulcabond benzene adds 100ml and contains 1g teicoplanin anhydrous pyridine solution, and 65～75 ℃ of stirring reactions are 10～12 hours under the nitrogen protection; filter; use pyridine; water; methyl alcohol; acetonitrile; washed with dichloromethane, behind the drying under reduced pressure with the rubigan isocyanates in anhydrous pyridine solution 110～120 ℃ the reaction 2～3 hours, after the filtration; use pyridine successively; water; methyl alcohol; acetone; the washed with dichloromethane drying gets teicoplanin rubigan isocyanate chiral chromatograph stationary-phase stuffing.
5, according to the preparation method of the described teicoplanin rubigan of claim 4 isocyanate chiral stationary phase filling, it is characterized in that: described glycopeptide class macrocyclic antibiotic is the rubigan isocyanate derivates of teicoplanin and teicoplanin.
6, according to the preparation method of the described teicoplanin rubigan of claim 4 isocyanate chiral stationary phase filling, it is characterized in that: described silica gel is chromatographic grade spherical silica gel or chromatographic grade amorphous silica gel.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102053449A (en) * | 2009-10-28 | 2011-05-11 | 中国科学院福建物质结构研究所 | Glutamic acid-derived chiral metal-organic nonlinear optical material |
| CN102824900A (en) * | 2012-08-28 | 2012-12-19 | 吉尔生化（上海）有限公司 | Method for chiral separation of various side chain protected amino acids |
| CN103816880A (en) * | 2014-03-05 | 2014-05-28 | 昆明医科大学 | Ginsenoside Rg1-phenyl isocyanate chiral stationary phase filler and preparation method thereof |
| CN103816879A (en) * | 2014-03-05 | 2014-05-28 | 昆明医科大学 | Ginsenoside Rg1-3,5-dimethyl phenyl isocyanate chiral stationary phase filler and preparation method thereof |
| CN104151450A (en) * | 2014-08-08 | 2014-11-19 | 北京师范大学 | Chiral pseudo-stationary phase for capillary electrochromatography, and preparation method for chiral pseudo-stationary phase |
| CN104275169A (en) * | 2013-07-01 | 2015-01-14 | 希施生物科技（上海）有限公司 | Method for chiral separation of various base amino acids |
| CN109999769A (en) * | 2019-03-11 | 2019-07-12 | 常州大学 | A kind of preparation method of the functional solid phase carrier for efficient separating Tryptophan enantiomer |
| CN112354519A (en) * | 2020-09-28 | 2021-02-12 | 南京江北新区生物医药公共服务平台有限公司 | Stationary phase containing phosphoramide structure and method for preparing protein mass spectrum capillary column |
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2006
- 2006-12-04 CN CNB2006101550127A patent/CN100571863C/en not_active Expired - Fee Related
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102053449A (en) * | 2009-10-28 | 2011-05-11 | 中国科学院福建物质结构研究所 | Glutamic acid-derived chiral metal-organic nonlinear optical material |
| CN102824900A (en) * | 2012-08-28 | 2012-12-19 | 吉尔生化（上海）有限公司 | Method for chiral separation of various side chain protected amino acids |
| CN104275169A (en) * | 2013-07-01 | 2015-01-14 | 希施生物科技（上海）有限公司 | Method for chiral separation of various base amino acids |
| CN103816880A (en) * | 2014-03-05 | 2014-05-28 | 昆明医科大学 | Ginsenoside Rg1-phenyl isocyanate chiral stationary phase filler and preparation method thereof |
| CN103816879A (en) * | 2014-03-05 | 2014-05-28 | 昆明医科大学 | Ginsenoside Rg1-3,5-dimethyl phenyl isocyanate chiral stationary phase filler and preparation method thereof |
| CN104151450A (en) * | 2014-08-08 | 2014-11-19 | 北京师范大学 | Chiral pseudo-stationary phase for capillary electrochromatography, and preparation method for chiral pseudo-stationary phase |
| CN109999769A (en) * | 2019-03-11 | 2019-07-12 | 常州大学 | A kind of preparation method of the functional solid phase carrier for efficient separating Tryptophan enantiomer |
| CN112354519A (en) * | 2020-09-28 | 2021-02-12 | 南京江北新区生物医药公共服务平台有限公司 | Stationary phase containing phosphoramide structure and method for preparing protein mass spectrum capillary column |
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