CN104001431A - Preparing method of beta-cyclodextrin immobilized cellulose membrane used for tryptophan chiral separation - Google Patents
Preparing method of beta-cyclodextrin immobilized cellulose membrane used for tryptophan chiral separation Download PDFInfo
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- CN104001431A CN104001431A CN201410102991.4A CN201410102991A CN104001431A CN 104001431 A CN104001431 A CN 104001431A CN 201410102991 A CN201410102991 A CN 201410102991A CN 104001431 A CN104001431 A CN 104001431A
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- 239000012528 membrane Substances 0.000 title claims abstract description 46
- 229920002678 cellulose Polymers 0.000 title claims abstract description 27
- 239000001913 cellulose Substances 0.000 title claims abstract description 27
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 title claims abstract description 20
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 title claims abstract description 19
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims abstract description 12
- 238000000926 separation method Methods 0.000 title abstract description 18
- 229920000858 Cyclodextrin Polymers 0.000 title abstract description 8
- 239000001116 FEMA 4028 Substances 0.000 title abstract description 4
- 235000011175 beta-cyclodextrine Nutrition 0.000 title abstract description 4
- 229960004853 betadex Drugs 0.000 title abstract description 4
- 239000000463 material Substances 0.000 claims abstract description 11
- 210000004379 membrane Anatomy 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims description 5
- 210000002469 basement membrane Anatomy 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 238000001471 micro-filtration Methods 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000006722 reduction reaction Methods 0.000 claims description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- 239000011148 porous material Substances 0.000 claims 1
- 238000001914 filtration Methods 0.000 abstract description 8
- QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical compound C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- 238000012986 modification Methods 0.000 abstract description 4
- 230000004048 modification Effects 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 229930182827 D-tryptophan Natural products 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 9
- 238000005194 fractionation Methods 0.000 description 7
- 229920002301 cellulose acetate Polymers 0.000 description 6
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 4
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 3
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 3
- 235000010413 sodium alginate Nutrition 0.000 description 3
- 239000000661 sodium alginate Substances 0.000 description 3
- 229940005550 sodium alginate Drugs 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 2
- 238000010382 chemical cross-linking Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005374 membrane filtration Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002994 phenylalanines Chemical class 0.000 description 2
- OGMGXKJQIOUTTB-FYZOBXCZSA-N (1r)-1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol;hydrobromide Chemical compound Br.OC1=C(O)C=C2[C@@H](C)NCCC2=C1 OGMGXKJQIOUTTB-FYZOBXCZSA-N 0.000 description 1
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 description 1
- 229930182832 D-phenylalanine Natural products 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 208000006735 Periostitis Diseases 0.000 description 1
- 241001415846 Procellariidae Species 0.000 description 1
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005557 chiral recognition Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 210000003460 periosteum Anatomy 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229940074569 salsolinol Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Separation Using Semi-Permeable Membranes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a preparing method of a beta-cyclodextrin immobilized cellulose membrane used for tryptophan chiral separation. According to the preparing method, the cellulose membrane is selected to be used as a base membrane material due to the advantages that the molecular structure per se of the cellulose membrane has multiple active hydroxyls capable of being used for modification, in addition, the price is low, and the acquisition is easy. Beta-cyclodextrin is chemically bonded on the cellulose membrane with the bore diameter of 0.22[mu]m, and chiral separation membranes are prepared. Racemic tryptophan is used as a separation object; in addition, separation effects are expressed; after the multilayer filtering, the modified filter membrane almost achieves the complete separation on DL-tryptophan; and a D-tryptophan solution is obtained. The separation performance stability RSD of the chiral membranes in 12h reaches 3.4 percent, and the stability is good. The preparing method can be widely applied to the field of chemical medicine separation.
Description
Technical field
The present invention relates to a kind of preparation method for tryptophan chiral resolution film, by synthetic and load, make the film for chiral resolution, can be widely used in chemical and medicine industry separation field.
Technical background
Membrane technology Split Method is to utilize contained particular separation functional site in film or outside film to split DL mixture.Membrane technology Split Method has that energy consumption is low, simple to operate, batch processing amount is large, easily continued operation, easily industry is amplified, device design is flexibly, in most cases the advantages such as ambient operation with system applies.According to the form of film, membrane technology Split Method is divided into liquid film fractionation and consolidates film and split two kinds.There is a common shortcoming that is difficult to overcome in chirality liquid film, i.e. less stable, and its commercial Application is very limited always.Chiral separation solid membrane stability is better, thereby becomes the primary study direction of embrane method chiral resolution.The solid film of chirality is divided into the solid film of body, the solid film of modification, solid film three classes of molecular engram by film material characteristic and preparation technology.The film material of the solid film of body is few, and use face is narrow.Molecular engram film selectivity is stronger, and every kind of molecular engram film can only split a kind of chiral material, preparation process complexity.And the designability of the solid film of modification is good, separative efficiency is high, uses widely, becomes the primary study direction of chiral separation solid film.
Beta-schardinger dextrin-has the following advantages as chiral selector tool: existing lot of documents report, and a large amount of chiral material that beta-schardinger dextrin-and derivative thereof successfully separate, is a kind of chiral resolving agent of extensive use; Beta-schardinger dextrin-can carry out reversible reacting with chiral material, and response intensity is suitable; The ph stability of beta-schardinger dextrin-is good.Utilize modification reaction by immobilized cyclodextrin above film, utilize film to separate and carry out chiral separation and caused people's attention.Su Cailian etc. support taking alumina ceramic membrane as passivation, β-CD is the solid film of chiral selector, fractionation object is D, L-Phe, after membrane filtration, utilize respectively UV to judge that it holds back the prepared film of difference preliminary judgement to two configurations phenylalanine is had to fractionation effect (Su Cailian D-phenylalanine and L-Phe, Dai Rongji, Tong Bin. cyclodextrin modified ceramic periosteum splits amino acid enantiomer. Second Committee membrane science and technology public lecture meeting paper .2005,09), Dai Rong continues etc. taking beta-schardinger dextrin-as chiral selector, ceramic membrane is basal lamina material, epoxychloropropane is crosslinking agent, split 1-methyl-6, 7-dihydroxy-1, 2, 3, 4, the prepared film of-tetrahydroisoquinoline is with the prolongation of time of penetration, chiral Recognition ability declines gradually, after about 9h, just reach balance, by the permeability test of a film unit, the ratio that makes the relative S-Salsolinol of R-salsolinol becomes 1.55 (Dai Rongji from original 0.87, Su Cailian, military petrel, Deng Yulin. beta-schardinger dextrin-chiral film separates 1-methyl-6, 7 beggar dihydroxy-1, 2, 3, 4,-tetrahydroisoquinoline .2008, 06, Beijing Institute of Technology's journal).Liu Shen etc. are taking β-CD as chiral selector, and adopting respectively cellulose acetate (CA) and sodium alginate (SA) is basal lamina material, prepares CA/ β-CD, SA/ β-CD chiral film by blending method.With α-CD, benzyl rings dextrin, p-methyl benzenesulfonic acid cyclodextrin, cyclodextrin water-soluble oligomer and 2,4-dimethyl beta-CD and cellulose acetate blend obtain chiral separation film, tryptophan Chiral Separation rate is respectively 6.57%, 7.58%, 7.85%, 8.02%, 8.59%, and the separation rate of phenylalanine enantiomer is respectively 7.68%, 9.33%, 9.07%, 9.57%, 9.85%.Reacted with β-CD and obtained chemical crosslinking film by CA, tryptophan and phenylalanine are split, its result shows: CA and β-CD chemical crosslinking film reach respectively 9.9% and 10.9% to the maximum separation rate of tryptophan and phenylalanine.(Liu Shen, Jin Zhimin, Wu Liguang; Preparation based on beta-schardinger dextrin-chiral film and the fractionation Master's thesis to tryptophan, phenylalanine enantiomer thereof, Zhejiang Polytechnical University; 2013 06 month).
Summary of the invention
The present invention is taking commercialization cellulose micro-filtration membrane as basal lamina material, and beta-schardinger dextrin-is chiral selector, and glutaraldehyde as cross linker is chemically bound in beta-schardinger dextrin-oligomer in cellulose micro-filtration membrane, makes the film for tryptophan chiral resolution.
The present invention compared with prior art tool has the following advantages: the immobilized cellulose membrane of beta-schardinger dextrin-only adopts the beta-schardinger dextrin-of underivatized, has simplified preparation process.Basal lamina material is common cellulose micro-filtration membrane, has saved production cost.The immobilized cellulose membrane of beta-schardinger dextrin-has strengthened film chiral resolution stability, has avoided chiral film prepared by blending method with carrying out of filtering and causes the loss of chiral selector.
Detailed description of the invention:
Below in conjunction with case study on implementation, feature of the present invention is described:
First prepare the immobilized cellulose membrane of beta-schardinger dextrin-by following steps, then the fractionation performance of sign and evaluated for film.
The step of preparing the immobilized cellulose membrane of beta-schardinger dextrin-is as follows:
(1) film pretreatment: 0.22 μ m cellulose filter membrane is put into 60mL pure water and soak 1h, pure water is poured out, filter membrane is for subsequent use.
(2) oxidation reaction: filter membrane is put into beaker, add periodic acid solution (0.25mM, 5mL), be placed in isothermal vibration 2h in constant temperature oscillator (25 DEG C, 150r/min).
(3) crosslinked immobilized reaction: after isothermal vibration 2h, periodic acid solution in beaker is poured out, with purified rinse water 3 times, contains sodium sulfate for subsequent use (0.7M), sulfuric acid (0.09M) and beta-schardinger dextrin-(0.1mM) mixed solution are poured in the beaker that filter membrane is housed, again glutaraldehyde solution (0.1mM) is under agitation added drop-wise in above-mentioned mixed solution gradually, reaction 2h in constant temperature oscillator (50 DEG C, 150r/min).
(4) reduction reaction: after isothermal vibration 2h, the beta-schardinger dextrin-in beaker and glutaraldehyde solution are poured out, used purified rinse water 3 times.By sodium cyanoborohydride (NaCNBH
3) solution (0.25mM) pours in the beaker that filter membrane is housed, isothermal vibration 2h in constant temperature oscillator (20 DEG C, 150r/min).
(5) after 2h, solution is poured out, used purified rinse water 3 times.Film is placed in water, and in refrigerator, 2 DEG C store for future use.
Performance characterization:
By the cross section (asking for an interview Fig. 2) of scanning electron microscopic observation cellulose membrane cross section (asking for an interview Fig. 1) and the immobilized cellulose membrane of beta-schardinger dextrin-, the cross section that contrasts rear discovery cellulose membrane cross section and the immobilized cellulose membrane of beta-schardinger dextrin-is obviously different, the latter cross section is more coarse, illustrate that beta-schardinger dextrin-and glutaraldehyde are cross-linked, beta cyclo dextrin polymer is immobilized on film.
Split effect evaluation method:
Taking racemic tryptophan as splitting object, racemic tryptophan solution (0.05g/L) carries out repeatedly one-way constant flow (0.1mL/min) in pressure-driven mode and filters on the miniature filter of flat sheet membrane, and this device effective filtration area is 36mm
2.High performance liquid chromatography (HPLC), for monitoring concentration and both concentration ratios of filtrate D-trp and L-Trp, is evaluated the fractionation effect (as shown in Figure 3) of tryptophan solution after chiral film multiple times of filtration.
Chiral separation performance:
(1) qualitative analysis: along with the increasing progressively of the filter membrane number of plies 2,4,6,8,10,12,14, the peak area of L-Trp little by little diminishes with respect to L-peak area in stoste as shown in Figure 3, and the peak area of D-trp is substantially constant.The peak area that front and back go out peak differs increase gradually, and after filtering the 14th layer, L-Trp configuration body almost disappears.This phenomenon can illustrate that the L-Trp configuration body cellulose membrane that is easily modified in split process holds back, and D-type body is difficult for being trapped, under pressure along with filtrate is flowed out, thereby realize the chiral resolution of tryptophan enantiomer, obtained only containing D-trp solution.
(2) quantitative analysis: enantiomeric excess value e.e. (%) is made to Fig. 4 as parameter:
The increase of filtering the number of plies, e.e. value is linear to be increased.Illustrate that multiple filtration post-modification filter membrane almost realized completely and to have split DL-Trp, obtain only containing D-trp solution.
The RSD of the fractionation performance repeatability of chiral film in 12h is 3.4%, and stability is better.
Brief description of the drawings
Fig. 1 is cellulose membrane cross section Electronic Speculum figure
Fig. 2 is the immobilized cellulose membrane cross section of beta-schardinger dextrin-Electronic Speculum figure
Fig. 3 tryptophan solution HPLC chromatogram after chirality membrane filtration
Fig. 4 enantiomer e.e. value and filtration number of plies relation curve.
Claims (3)
1. the preparation method who the invention provides a kind of immobilized cellulose membrane of beta-schardinger dextrin-for tryptophan chiral resolution, the method is divided following steps:
(1) first carry out film pretreatment: average pore size 0.1-0.8 μ m cellulose filter membrane is put into pure water and soak 0.5-2 hour;
(2) filter membrane is put into 0.1-0.4mM periodic acid solution, 15-40 DEG C of isothermal vibration 1-3 hour;
(3) with pure water, film is cleaned, again film is immersed to for subsequent use containing in 0.35-1.7M sodium sulphate, 0.028-1.9M sulfuric acid and 0.05-2.5mM beta-schardinger dextrin-mixed solution, again 0.03-0.15mM glutaraldehyde solution is under agitation added drop-wise in above-mentioned mixed solution gradually, at 15-40 DEG C of isothermal vibration reaction 2-3 hour;
(4) reduction reaction: after film being rinsed well with pure water, film is immersed in 0.1-0.4mM sodium cyanoborohydride solution to 15-40 DEG C of isothermal vibration 2h;
(5) with pure water, film is cleaned and is placed in water, under 1-5 DEG C of condition, store.
2. the preparation method of a kind of immobilized cellulose membrane of beta-schardinger dextrin-for tryptophan chiral resolution according to claim 1, is characterized in that the described immobilized cellulose membrane of beta-schardinger dextrin-only adopts underivatized beta-schardinger dextrin-, has simplified preparation process.
3. the preparation method of a kind of immobilized cellulose membrane of beta-schardinger dextrin-for tryptophan chiral resolution according to claim 1, is characterized in that described basal lamina material is common cellulose micro-filtration membrane, has saved production cost.
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| CN104826506A (en) * | 2015-05-18 | 2015-08-12 | 天津工业大学 | Beta-cyclodextrin grafted polymer chiral separation membrane and preparation method thereof |
| CN105021681A (en) * | 2015-07-08 | 2015-11-04 | 常州大学 | Chitosan-modified glassy carbon electrode-based selective recognition of tryptophan enantiomer containing zinc ion |
| CN106928378A (en) * | 2017-03-29 | 2017-07-07 | 中国药科大学 | A kind of preparation method of dodecanoyl beta cyclodextrin and the preparation method of the PS membrane for tryptophan chiral resolution |
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