CN110257362A - The preparation method and application of a kind of cholic acid and its surfactant modified metal organic framework nano-composite catalyst of derivative - Google Patents
The preparation method and application of a kind of cholic acid and its surfactant modified metal organic framework nano-composite catalyst of derivative Download PDFInfo
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- CN110257362A CN110257362A CN201910481687.8A CN201910481687A CN110257362A CN 110257362 A CN110257362 A CN 110257362A CN 201910481687 A CN201910481687 A CN 201910481687A CN 110257362 A CN110257362 A CN 110257362A
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- cholic acid
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- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 title claims abstract description 35
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 title claims abstract description 35
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 239000004380 Cholic acid Substances 0.000 title claims abstract description 34
- 229960002471 cholic acid Drugs 0.000 title claims abstract description 34
- 235000019416 cholic acid Nutrition 0.000 title claims abstract description 34
- 239000003054 catalyst Substances 0.000 title claims abstract description 30
- 239000012621 metal-organic framework Substances 0.000 title claims abstract description 29
- 239000002114 nanocomposite Substances 0.000 title claims abstract description 23
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 102000004190 Enzymes Human genes 0.000 claims abstract description 39
- 108090000790 Enzymes Proteins 0.000 claims abstract description 39
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000000243 solution Substances 0.000 claims abstract description 16
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 12
- 239000007864 aqueous solution Substances 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims abstract description 10
- 238000002156 mixing Methods 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000009777 vacuum freeze-drying Methods 0.000 claims abstract description 7
- 239000008367 deionised water Substances 0.000 claims abstract description 6
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 6
- 239000012266 salt solution Substances 0.000 claims abstract description 4
- SMEROWZSTRWXGI-HVATVPOCSA-N lithocholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 SMEROWZSTRWXGI-HVATVPOCSA-N 0.000 claims description 32
- 238000006555 catalytic reaction Methods 0.000 claims description 12
- 239000003876 biosurfactant Substances 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- SMEROWZSTRWXGI-UHFFFAOYSA-N Lithocholsaeure Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 SMEROWZSTRWXGI-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 6
- 238000005119 centrifugation Methods 0.000 claims description 6
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 claims description 3
- 229960001091 chenodeoxycholic acid Drugs 0.000 claims description 3
- 150000002460 imidazoles Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229940045946 sodium taurodeoxycholate Drugs 0.000 claims description 3
- YXHRQQJFKOHLAP-FVCKGWAHSA-M sodium;2-[[(4r)-4-[(3r,5r,8r,9s,10s,12s,13r,14s,17r)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonate Chemical compound [Na+].C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 YXHRQQJFKOHLAP-FVCKGWAHSA-M 0.000 claims description 3
- IYVYLVCVXXCYRI-UHFFFAOYSA-N 1-propylimidazole Chemical compound CCCN1C=CN=C1 IYVYLVCVXXCYRI-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 claims description 2
- LVOASPZGXNAHJI-UHFFFAOYSA-N 4-imidazol-1-ylaniline Chemical class C1=CC(N)=CC=C1N1C=NC=C1 LVOASPZGXNAHJI-UHFFFAOYSA-N 0.000 claims description 2
- XDKUKGIJDNUFGK-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CN=C[N]1 XDKUKGIJDNUFGK-UHFFFAOYSA-N 0.000 claims description 2
- 102000004882 Lipase Human genes 0.000 claims description 2
- 108090001060 Lipase Proteins 0.000 claims description 2
- 239000004367 Lipase Substances 0.000 claims description 2
- VIHYIVKEECZGOU-UHFFFAOYSA-N N-acetylimidazole Chemical compound CC(=O)N1C=CN=C1 VIHYIVKEECZGOU-UHFFFAOYSA-N 0.000 claims description 2
- -1 NaTDC Chemical compound 0.000 claims description 2
- 108091005804 Peptidases Proteins 0.000 claims description 2
- 102000011420 Phospholipase D Human genes 0.000 claims description 2
- 108090000553 Phospholipase D Proteins 0.000 claims description 2
- 102000015439 Phospholipases Human genes 0.000 claims description 2
- 108010064785 Phospholipases Proteins 0.000 claims description 2
- 239000004365 Protease Substances 0.000 claims description 2
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 2
- 102000014384 Type C Phospholipases Human genes 0.000 claims description 2
- 108010079194 Type C Phospholipases Proteins 0.000 claims description 2
- 235000019421 lipase Nutrition 0.000 claims description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 101710098554 Lipase B Proteins 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- WVULKSPCQVQLCU-BUXLTGKBSA-N glycodeoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 WVULKSPCQVQLCU-BUXLTGKBSA-N 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 9
- 230000003197 catalytic effect Effects 0.000 abstract description 8
- 230000008859 change Effects 0.000 abstract description 4
- 239000008346 aqueous phase Substances 0.000 abstract description 3
- 238000011084 recovery Methods 0.000 abstract description 2
- 239000013154 zeolitic imidazolate framework-8 Substances 0.000 description 39
- MFLKDEMTKSVIBK-UHFFFAOYSA-N zinc;2-methylimidazol-3-ide Chemical compound [Zn+2].CC1=NC=C[N-]1.CC1=NC=C[N-]1 MFLKDEMTKSVIBK-UHFFFAOYSA-N 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- 102000018120 Recombinases Human genes 0.000 description 3
- 108010091086 Recombinases Proteins 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000002086 nanomaterial Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000003613 bile acid Substances 0.000 description 2
- 239000003833 bile salt Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229940099352 cholate Drugs 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 1
- 229960003964 deoxycholic acid Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000105 evaporative light scattering detection Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- 102000034238 globular proteins Human genes 0.000 description 1
- 108091005896 globular proteins Proteins 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 125000003219 lithocholic acid group Chemical group 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
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- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
- C12N9/18—Carboxylic ester hydrolases (3.1.1)
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- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
- C12N9/18—Carboxylic ester hydrolases (3.1.1)
- C12N9/20—Triglyceride splitting, e.g. by means of lipase
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- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/48—Hydrolases (3) acting on peptide bonds (3.4)
- C12N9/50—Proteinases, e.g. Endopeptidases (3.4.21-3.4.25)
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- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/001—Amines; Imines
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- C12Y301/01—Carboxylic ester hydrolases (3.1.1)
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- C12Y301/04—Phosphoric diester hydrolases (3.1.4)
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- C12Y301/00—Hydrolases acting on ester bonds (3.1)
- C12Y301/04—Phosphoric diester hydrolases (3.1.4)
- C12Y301/04004—Phospholipase D (3.1.4.4)
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Abstract
The invention discloses the preparation methods and application of a kind of cholic acid and its surfactant modified metal organic framework nano-composite catalyst of derivative.The preparation method is the following steps are included: match imidazole and its derivants aqueous solution, and at room temperature, the free enzyme solution of dropwise addition while stirring obtains mixed liquor 1；Into mixed liquor 1, side stirring change is added dropwise metal ion salt solution and obtains mixed liquor 2, cholic acid and its derivative solution are then rapidly added into mixed liquor 2 in 1min, 30-60min is stirred, be centrifuged and is rinsed 1-3 times with deionized water, vacuum freeze drying to constant weight.And have studied application of the catalyst in biocatalysis.The present invention is prepared using aqueous phase solution mixing method, easy to operate, the period is short, mild condition, low in cost, enzyme stability is high, the enzyme rate of recovery is high, carrier enzyme molecule bond strength is high, has both biology and physics catalytic activity.
Description
Technical field
The invention belongs to the technique for fixing fields of enzyme, and in particular to a kind of cholic acid and its surfactant modified gold of derivative
Belong to the preparation method and application of organic backbone nano-composite catalyst.
Background technique
Enzyme reaction carries out in aqueous solution, but there is also many problems, such as resolvase are more unstable in aqueous phase system,
Under the influence of the extraneous factors such as high temperature, soda acid, enzyme mutability inactivation；After substrate and enzyme reaction are complete, even if enzyme activity remains unchanged
Maintain higher level, it is also difficult to it recycles and reuses, and enzyme is used as impurity and product to mix after the completion of reaction, this
Difficulty not only is brought to the separation in later period and purifying, also increases industrial cost.Enzyme immobilization technology, which refers to, bears enzyme
It is loaded on suitable carrier, and keeps the high catalytic activity of enzyme.Compared with resolvase, immobilised enzymes maintain its efficiently it is single-minded and
While mild enzymic catalytic reaction characteristic, also have good operational stability and storage stability, be easily isolated and recycle,
The advantages that operating continuous controllable, reusable and simple process, advantage is significant in industrial application.
However currently, the research report of the immobilization in relation to PLB both at home and abroad is less, this greatly limits the industry of PLB
Change production application.Since nano material possesses how species specific biology performance, at present in biological medicine and Industrial Catalysis etc.
Field has been widely used, and the nano material containing metal ion is also widely used in enzyme immobilizatio field.Metal
With the amino acid in enzyme molecule coordination or electrostatic interaction can occur for ion, and enzyme molecule is allowed to be attached to nano material
Surface, thus a large amount of enzyme molecule can be made to be also mounted on material while keeping its conformation and vigor.In addition, nanometer
To enzyme activity, there are also positive facilitations under certain specific conditions for metal ion in material.MOFs is a kind of with good suction
The porous material of attached performance has broad application prospects in fields such as biology, catalysis, can also be used as a kind of ideal fixation
Change the carrier of enzyme.However, zymoprotein is often macromolecular structure, therefore there is more large aperture to obtain by modified MOFs material
Material the fixed network of enzyme have important researching value.
Surfactant can reduce by two alternate interfacial tensions, while can also increase the mobility of water-insoluble substrate
And dissolubility.In addition to this, surfactant can prevent the conformation of zymoprotein from wrecking in catalytic process, can play
Enhance the effect of enzyme molecule stability.Bile salt is a kind of potential biosurfactant, can be used as certain nonpolar materials
The solubilizer and emulsifier of material, such as the substrate PC of this project, its solubility in water are lower.Herein using bile salt biology
Surfactant come modify MOFs material (ZIF-8 material) carry out PLB immobilization research, simply have studied fixation support with
And influence of the fixing condition to immobilization.Its immobilization process schematic diagram is as shown in Figure 1.
Summary of the invention
In view of the deficiencies of the prior art, the purpose of the present invention is to provide a kind of cholic acid and its derivative surfactant to repair
The preparation method and application of metal organic framework nano-composite catalyst are adornd, this method is prepared using aqueous phase solution mixing method, behaviour
Work is simple, the period is short, mild condition, low in cost, enzyme stability is high, the enzyme rate of recovery is high, carrier enzyme molecule bond strength is high, simultaneous
Standby biology and physics catalytic activity.
In order to solve the above technical problems, the technical scheme adopted by the invention is as follows:
A kind of preparation method of cholic acid and its surfactant modified metal organic framework nano-composite catalyst of derivative, including
Following steps:
Step 1, the preparation of metal organic framework nano-composite catalyst
With 0.5-2.5 mol/L imidazole and its derivants aqueous solution, at room temperature, free enzyme solution is added dropwise while stirring, is mixed
Liquid 1, then 0.2-0.6 mol/L metal ion salt solution is added dropwise while stirring into mixed liquor 1, obtain mixed liquor 2；
Step 2, cholic acid and its surfactant modified metal organic framework nano-composite catalyst of derivative
It obtains in the 1min of mixed liquor 2, cholic acid and its derivative that 10mmol/L-100mmol/L is added into mixed liquor 2 are molten
Liquid obtains cholic acid/metal organic framework nano-composite catalyst aqueous solution after stirring 30-60min at room temperature, and filter residue is used after centrifugation
Deionized water is rinsed 1-3 times, and vacuum freeze drying to constant weight is to get nano-composite catalyst.
It is that selected imidazole and its derivants are 2-methylimidazole, benzimidazole, 4- methyl in step 1 as improved
Imidazoles, 2,4- methylimidazole, N- acetyl imidazole, 1- (4- aminophenyl) imidazoles or N- propyl imidazole, or derivatives thereof in
It is a kind of；The concentration of imidazole and its derivants is 1.25 mol/L, and additive amount is 25 mmol, and mixing speed is 100~150rpm.
It is that metal ion described in step 1 is Zn as improved2+Or Co2+, the concentration of metal ion is 0.31mol/
L, mixing speed are 100~150rpm.
It is that the cholic acid and its derivative are lithocholic acid, NaTDC as improved, sodium taurodeoxycholate is sweet
Ammonia deoxycholic acid receives or one of chenodesoxycholic acid sodium, and the solute for the enzyme solution that dissociates is lipase, protease, phospholipase A, phosphatide
Any one in enzyme B, phospholipase C or phospholipase D.
It is that the concentration of cholic acid and its derivative solution is 20 mmol/L, additive amount 2 in step 2 as improved
Mmol, centrifugal speed 7000rpm, centrifugation time 15min, the vacuum degree of vacuum freeze drying are 1.3~13Pa, temperature
It is -85 DEG C~-10 DEG C.
Above-mentioned cholic acid and its surfactant modified metal organic framework nano-composite catalyst of derivative are in biocatalysis
In application.
It is that above-mentioned application adds the following steps are included: weigh the raw material containing phosphatidyl choline in centrifuge tube as improved
Enter deionized water, cholic acid biosurfactant modified metal organic backbone nano-composite catalyst is added, in water-bath
Glycerol production phosphatidyl choline is obtained after being stirred to react 2-6 h.
The utility model has the advantages that
Compared with prior art, the present invention provides a kind of cholic acid and its surfactant modified metal organic framework of derivative to receive
The preparation method and application of rice composite catalyst, the preparation method is easy to operate, the period is short, low in cost, reaction condition is mild,
Carrier enzyme molecule bond strength is high, and improves the stability and activity of enzyme in catalyst, and gained catalyst has both biology and object
Catalytic activity is managed, aqueous catalysis, organic solvent, biphasic catalysis reaction field are especially suitable for.
Detailed description of the invention
Fig. 1 is the flow chart of immobilization process of the present invention；
Fig. 2 is the scanning electron microscope (SEM) photograph and transmission electron microscope picture of the resulting catalyst of embodiment 1, wherein the scanning electron microscope of (A) ZIF-8
Figure, the scanning electron microscope (SEM) photograph of (B) PLB/ZIF-8, the scanning electron microscope (SEM) photograph of (C) LCA@ZIF-8, the scanning electricity of (D) LCA@PLB/ZIF-8
Mirror figure, the transmission electron microscope picture of (a) ZIF-8, (b) transmission electron microscope picture of PLB/ZIF-8, (c) transmission electron microscope picture of LCA@ZIF-8,
(d) transmission electron microscope picture of LCA@PLB/ZIF-8；
Fig. 3 is resolvase (Free PLB), enzyme/metal organic framework (PLB/ZIF-8), lithocholic acid/enzyme/metal organic framework
The catalytic efficiency comparison diagram of (LCA@PLB/ZIF-8)；
Fig. 4 is the infrared characterization chart of Free PLB, PLB/ZIF-8, LCA@PLB/ZIF-8；
Fig. 5 is the recycling rate of waterused figure of PLB/ZIF-8, LCA@PLB/ZIF-8.
Fig. 6 is the application drawing of Free PLB, LCA@PLB/ZIF-8.
Specific embodiment
Embodiment 1
A kind of preparation method of cholic acid and its derivative biosurfactant modified metal organic backbone nano-composite catalyst,
The following steps are included:
Step 1, the preparation of metal organic framework nano-composite catalyst
With 0.5-2.5 mol/L imidazoles aqueous solution, at room temperature, free enzyme solution is added dropwise while stirring, side stirring becomes into mixed liquor
0.2-0.6 mol/L metal ion salt solution is added dropwise.
Step 2, cholic acid and its modified trip metal organic framework nano-composite catalyst of derivative biosurfactant
The cholic acid and its derivative solution of 10mmol/L-100mmol/L are rapidly added into mixed liquor.30- is stirred at room temperature
Cholic acid/enzyme/metal organic framework nano-composite catalyst aqueous solution is obtained after 60min；It is centrifuged and rinses 1-3 with deionized water
It is secondary, vacuum freeze drying to constant weight.
It is that the surfactant is lithocholic acid, NaTDC, sodium taurodeoxycholate as improved, sweet ammonia is de-
Oxycholic acid is received, one of chenodesoxycholic acid sodium, and the solute for the enzyme solution that dissociates is one of phosphatidase.
It is that the concentration of 2-methylimidazole is 1.25 mol/L in step 1 as improved, the additive amount of 2-methylimidazole is
25 mmol, mixing speed are 100~150rpm.
It is that metal ion described in step 1 is Zn as improved2+、Co2+One of which in, concentration are
0.31mol/L, mixing speed are 100~150rpm.
It is that surfactant described in step 2 is lithocholic acid as improved.
Further improved to be, the concentration of surfactant is 20mmol/L in step 2, and the additive amount of surfactant is
2 mmol, centrifugal speed 7000rpm, centrifugation time 15min, the vacuum degree of vacuum freeze drying are 1.3~13Pa, temperature
It is -85 DEG C~-10 DEG C.
As shown in Fig. 2, granatohedron is presented in metal organic framework nano-complex (ZIF-8) manufactured in the present embodiment
Form, average particle size distribution is in 580 nm or so, and metal organic framework nano-composite catalyst (PLB/ZIF-8) presentation is not advised
Then spherical structure, particle diameter distribution is in 250 nm or so, cholic acid and its organic bone of derivative biosurfactant modified metal
The phenomenon that reuniting is presented in frame nano-complex (LCA@ZIF-8), and average particle size distribution is in 74 nm or so, and cholic acid and its derivative
The spherical mixed of reunion is presented in object biosurfactant modified metal organic backbone nano-composite catalyst (LCA@PLB/ZIF-8)
Structure is closed, average particle size distribution is in 130 nm or so.This is because, the property of lithocholic acid itself is also easy to produce agglomeration, and
After protein is added, charge, meeting and LCA, Zn are also carried on spherical protein molecule surface2+With 2-methylimidazole phase interaction
With so that material changes toward spherical structure direction.
In order to further verify whether PLB is successfully embedded in inside LCA@ZIF-8 and ZIF-8, LCA@PLB/ is tested
Fourier's infared spectrum of ZIF-8, LCA@ZIF-8, PLB/ZIF-8 and ZIF-8.As shown in figure 3, LCA@PLB/ZIF-8 and
PLB/ZIF-8 is in 1645cm-1There is the vibration peak of acyl group C=O in place, it was demonstrated that PLB has successfully been fixed on LCA@PLB/
Inside ZIF-8 and PLB/ZIF-8.
Embodiment 2
Have studied the comparison of Free PLB, PLB/ZIF-8 and LCA@PLB/ZIF-8 catalytic activity
LCA is one of component of bile acid, and bile acid is the final product of mammal cholesterol catabolism, the gallbladder formed
Juice hydrochlorate is a kind of biosurfactant for having special construction and possessing unusual characteristic, can contribute to dissolved fat
With the substance of the slightly solubilities such as liposoluble vitamin.Cholate can be used as in pharmaceutical preparation as soluble amphipathic compound
Sorbefacient, in addition to this, it is also used as the excipient of enzyme stability.In addition, it can also be with bivalent metal ion
A series of different nano-complex of structures of different sizes is formed by metal coordination.Lithocholic acid dressing agent as shown in Figure 3
Addition to enzyme activity have it is preferable promote effect, compared with unmodified PLB/ZIF-8, enzyme activity improves 126% or so.
Embodiment 3
Have studied the recycling rate of waterused of PLB/ZIF-8 and LCA@PLB/ZIF-8
Although the structure of PLB/ZIF-8 and LCA@PLB/ZIF-8 can be in catalysis reaction and centrifugation during recycling
By mechanical damage and the inactivation of enzyme during washing, but after reusing 10 continuous circulations, find PLB/
The residual activity of ZIF-8 is still 70% or more, and the residual activity of LCA@PLB/ZIF-8 maintains 80% or more.It therefore can be big
The big totle drilling cost for reducing industrial application.However Free PLB is in aqueous solution, is difficult to carry out by general isolation technics means
Recycling repeatedly uses, and increases the cost of industrial application.
Embodiment 4
With the resulting cholic acid of embodiment 1 and its derivative biosurfactant modified metal organic backbone nano-composite catalyst
It is applied in water phase, for catalyzing and synthesizing the research of glycerolphosphocholine.
The application is added lecithin (20g/L) the following steps are included: in the reaction solution of 5mL, and the free of 100 μ L is added
PLA1Or LCA@PLB/ZIF-8 and PLB/ZIF-8 containing equal protein content.The magnetic agitation in 40 °C of water-bath
(600 rpm) 8 h use the yield of high performance liquid chromatography measurement glycerolphosphocholine.
It extracts reaction solution 200 μ L to be dissolved in the methanol solution liquid of 1 mL, and uses 0.22 μm of nylon membrane filtered dilutions,
To remove insoluble matter.Filtrate is dried in nitrogen atmosphere and carries out analysis measurement in HPLC-ELSD.Chromatographic column is silica gel
Column (250 mm × 4.6 mm, 5 μm), mobile phase are methanol and aqueous solution (v:v=90:10), and flow velocity is 1.0 mL/min, post case
Temperature is controlled at 25 °C.
Embodiment 5
The otherness of free PLB and LCA@PLB/ZIF-8 catalytic efficiency are studied, investigation compared PLB, LCA@PLB/ZIF-8 is urged
Change the yield that phosphatidyl choline generates glycerolphosphocholine.
Compared with Free PLB, for LCA@PLB/ZIF-8 under different concentration of substrate, the yield and efficiency of catalysate are high
In Free PLB, when concentration of substrate is 60 g/L, in the reaction system of LCA@PLB/ZIF-8 catalyst, the yield of L- α-GPC and
Conversion ratio reaches maximum, and for maximum conversion rate 97% or so, maximum output reaches 19.91 g/L；Compared with Free PLB, turn
Rate improves 7% or so, output increased 17% or so.
Claims (7)
1. the preparation method of a kind of cholic acid and its surfactant modified metal organic framework nano-composite catalyst of derivative,
It is characterized in that, comprising the following steps:
Step 1, the preparation of metal organic framework nano-composite catalyst
With 0.5-2.5 mol/L imidazole and its derivants aqueous solution, at room temperature, free enzyme solution is added dropwise while stirring, is mixed
Liquid 1, then 0.2-0.6 mol/L metal ion salt solution is added dropwise while stirring into mixed liquor 1, obtain mixed liquor 2；
Step 2, cholic acid and its surfactant modified metal organic framework nano-composite catalyst of derivative
It obtains in the 1min of mixed liquor 2, cholic acid and its derivative that 10mmol/L-100mmol/L is added into mixed liquor 2 are molten
Liquid obtains cholic acid/metal organic framework nano-composite catalyst aqueous solution after stirring 30-60min at room temperature, and filter residue is used after centrifugation
Deionized water is rinsed 1-3 times, and vacuum freeze drying to constant weight is to get nano-composite catalyst.
2. cholic acid according to claim 1 and its nano combined catalysis of the surfactant modified metal organic framework of derivative
The preparation method of agent, which is characterized in that selected imidazole and its derivants are 2-methylimidazole, benzimidazole, 4- first in step 1
Base imidazoles, 2,4- methylimidazole, N- acetyl imidazole, 1- (4- aminophenyl) imidazoles or N- propyl imidazole, or derivatives thereof
Middle one kind；The concentration of imidazole and its derivants be 1.25 mol/L, additive amount be 25 mmol, mixing speed be 100~
150rpm。
3. cholic acid according to claim 1 and its nano combined catalysis of the surfactant modified metal organic framework of derivative
The preparation method of agent, which is characterized in that metal ion described in step 1 is Zn2+Or Co2+, the concentration of metal ion is
0.31mol/L, mixing speed are 100~150rpm.
4. cholic acid according to claim 1 and its nano combined catalysis of the surfactant modified metal organic framework of derivative
The preparation method of agent, which is characterized in that the cholic acid and its derivative are lithocholic acid, NaTDC, sodium taurodeoxycholate,
Glycodesoxycholic acid receives or one of chenodesoxycholic acid sodium, and the solute for the enzyme solution that dissociates is lipase, protease, phospholipase A, phosphorus
Any one in lipase B, phospholipase C or phospholipase D.
5. cholic acid according to claim 1 and its nano combined catalysis of the surfactant modified metal organic framework of derivative
The preparation method of agent, which is characterized in that the concentration of cholic acid and its derivative solution is 20 mmol/L, additive amount 2 in step 2
Mmol, centrifugal speed 7000rpm, centrifugation time 15min, the vacuum degree of vacuum freeze drying are 1.3~13Pa, temperature
It is -85 DEG C~-10 DEG C.
6. being based on cholic acid described in claim 1 and its nano combined catalysis of the surfactant modified metal organic framework of derivative
Application of the agent in biocatalysis.
7. application according to claim 6, which comprises the following steps: weigh the raw material containing phosphatidyl choline
In centrifuge tube, deionized water is added, adds the nano combined catalysis of cholic acid biosurfactant modified metal organic backbone
Agent obtains glycerol production phosphatidyl choline after being stirred to react 2-6 h in water-bath.
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