CN105087537B - 一种7-aca固定化酶lk118的制备及其使用方法 - Google Patents
一种7-aca固定化酶lk118的制备及其使用方法 Download PDFInfo
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- CN105087537B CN105087537B CN201510587330.XA CN201510587330A CN105087537B CN 105087537 B CN105087537 B CN 105087537B CN 201510587330 A CN201510587330 A CN 201510587330A CN 105087537 B CN105087537 B CN 105087537B
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- 102000004190 Enzymes Human genes 0.000 title claims abstract description 94
- 108090000790 Enzymes Proteins 0.000 title claims abstract description 83
- 238000000034 method Methods 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 title claims description 78
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 108700023418 Amidases Proteins 0.000 claims abstract description 21
- 102000005922 amidase Human genes 0.000 claims abstract description 21
- 239000004593 Epoxy Substances 0.000 claims description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 238000006555 catalytic reaction Methods 0.000 claims description 12
- 239000002250 absorbent Substances 0.000 claims description 10
- 230000002745 absorbent Effects 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 9
- 239000011347 resin Substances 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 9
- 239000012141 concentrate Substances 0.000 claims description 8
- 239000008055 phosphate buffer solution Substances 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 239000003431 cross linking reagent Substances 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 239000008363 phosphate buffer Substances 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 241000589774 Pseudomonas sp. Species 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000010557 suspension polymerization reaction Methods 0.000 claims description 3
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000000872 buffer Substances 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 230000002255 enzymatic effect Effects 0.000 abstract description 7
- 230000009089 cytolysis Effects 0.000 abstract description 5
- 230000008569 process Effects 0.000 abstract description 4
- 239000003086 colorant Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 28
- 238000004519 manufacturing process Methods 0.000 description 11
- -1 propylene glycol dimethyl propylene Olefin Chemical class 0.000 description 6
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000002924 oxiranes Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- IXUSDMGLUJZNFO-BXUZGUMPSA-N (7R)-7-(4-carboxybutanamido)cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCCC(O)=O)[C@@H]12 IXUSDMGLUJZNFO-BXUZGUMPSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 229930186147 Cephalosporin Natural products 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 229940124587 cephalosporin Drugs 0.000 description 2
- 150000001780 cephalosporins Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- HBGPNLPABVUVKZ-POTXQNELSA-N (1r,3as,4s,5ar,5br,7r,7ar,11ar,11br,13as,13br)-4,7-dihydroxy-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1h-cyclopenta[a]chrysen-9-one Chemical compound C([C@@]12C)CC(=O)C(C)(C)[C@@H]1[C@H](O)C[C@]([C@]1(C)C[C@@H]3O)(C)[C@@H]2CC[C@H]1[C@@H]1[C@]3(C)CC[C@H]1C(=C)C HBGPNLPABVUVKZ-POTXQNELSA-N 0.000 description 1
- PFRGGOIBYLYVKM-UHFFFAOYSA-N 15alpha-hydroxylup-20(29)-en-3-one Natural products CC(=C)C1CCC2(C)CC(O)C3(C)C(CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C12 PFRGGOIBYLYVKM-UHFFFAOYSA-N 0.000 description 1
- OYIFNHCXNCRBQI-UHFFFAOYSA-N 2-aminoadipic acid Chemical group OC(=O)C(N)CCCC(O)=O OYIFNHCXNCRBQI-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 108700016155 Acyl transferases Proteins 0.000 description 1
- BBJLVBHQJYDCHY-UHFFFAOYSA-N C(C=C)(=O)O.CC(O)(C(CO)(CO)CO)C Chemical compound C(C=C)(=O)O.CC(O)(C(CO)(CO)CO)C BBJLVBHQJYDCHY-UHFFFAOYSA-N 0.000 description 1
- 229920001241 Cyamelide Polymers 0.000 description 1
- SOKRNBGSNZXYIO-UHFFFAOYSA-N Resinone Natural products CC(=C)C1CCC2(C)C(O)CC3(C)C(CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C12 SOKRNBGSNZXYIO-UHFFFAOYSA-N 0.000 description 1
- IGSVRQINSVGVTL-DOIPELPJSA-N [(2r,3r,4s,5r)-2,3,4,5-tetrakis(2-methylprop-2-enoyloxy)-6-oxohexyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC[C@@H](OC(=O)C(C)=C)[C@@H](OC(=O)C(C)=C)[C@H](OC(=O)C(C)=C)[C@@H](OC(=O)C(C)=C)C=O IGSVRQINSVGVTL-DOIPELPJSA-N 0.000 description 1
- ZCZFEIZSYJAXKS-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COC(=O)C=C ZCZFEIZSYJAXKS-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 102000045404 acyltransferase activity proteins Human genes 0.000 description 1
- 108700014220 acyltransferase activity proteins Proteins 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
Landscapes
- Enzymes And Modification Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
Abstract
Description
收率% | 纯度% | 残留CPC% | 色级 | |
实施例一 | 60.2 | 99.2 | 0.12 | 1# |
实施例二 | 60.3 | 99.3 | 0.08 | 1# |
实施例三 | 60.2 | 99.4 | 0.07 | 1# |
实施例四 | 60.4 | 99.2 | 0.09 | 1# |
Claims (5)
Priority Applications (1)
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CN201510587330.XA CN105087537B (zh) | 2015-09-16 | 2015-09-16 | 一种7-aca固定化酶lk118的制备及其使用方法 |
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CN201510587330.XA CN105087537B (zh) | 2015-09-16 | 2015-09-16 | 一种7-aca固定化酶lk118的制备及其使用方法 |
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CN105087537A CN105087537A (zh) | 2015-11-25 |
CN105087537B true CN105087537B (zh) | 2018-09-28 |
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Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN106434616A (zh) * | 2016-12-19 | 2017-02-22 | 山东思科新材料有限公司 | 一种白酒用固定化增酯酶的制备及应用方法 |
CN111876402A (zh) * | 2020-06-30 | 2020-11-03 | 伊犁川宁生物技术有限公司 | 一种固定化头孢菌素c酰化酶的制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102827912A (zh) * | 2012-08-31 | 2012-12-19 | 山东鲁抗立科药业有限公司 | 两酶一步法制备医药中间体d-7-aca的工艺 |
CN103436517A (zh) * | 2013-09-05 | 2013-12-11 | 北京科技大学 | 一种制备固定化头孢菌素c酰化酶的方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100530299B1 (ko) * | 2003-08-11 | 2005-11-22 | 산도즈 게엠베하 | 변이 세팔로스포린 c 아실라제 및 이를 이용한 7-aca 제조방법 |
-
2015
- 2015-09-16 CN CN201510587330.XA patent/CN105087537B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102827912A (zh) * | 2012-08-31 | 2012-12-19 | 山东鲁抗立科药业有限公司 | 两酶一步法制备医药中间体d-7-aca的工艺 |
CN103436517A (zh) * | 2013-09-05 | 2013-12-11 | 北京科技大学 | 一种制备固定化头孢菌素c酰化酶的方法 |
Non-Patent Citations (4)
Title |
---|
Characteristic of immobilized cephalosporin C acylase and its application in one-step enzymatic conversion of cephalosporin C to 7-aminocephalosporanic acid;Xiangwei Zhu 等;《World J Microbiol Biotechnol》;20100810;第27卷;第823-829页,尤其是题目、摘要、第824页左栏第二段、第824页右栏Immobilization of CPC acylase onto epoxy supports部分、第825页左栏最后一段到右栏第一段、826页右栏第二段到第828页左栏第二段、第827页Fig.3-5 * |
固定化酶技术及其在医药上的应用新进展;杨杰 等;《药学生物技术》;20131231;第20卷(第4期);第553-556页 * |
酶法合成7-ACA及头孢菌素类抗生素的研究进展;芮菊 等;《2008年中国药学会学术年会暨第八届中国药师周论文集》;20081231;第545-550页 * |
酶法转化头孢菌素C成为7-氨基头孢烷酸的研究进展;刘福强 等;《山东食品发酵》;20091231;第17-20页 * |
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