CN1111604C - Process for preparing D-lactone valerate by microbe enzyme method - Google Patents
Process for preparing D-lactone valerate by microbe enzyme method Download PDFInfo
- Publication number
- CN1111604C CN1111604C CN 01104070 CN01104070A CN1111604C CN 1111604 C CN1111604 C CN 1111604C CN 01104070 CN01104070 CN 01104070 CN 01104070 A CN01104070 A CN 01104070A CN 1111604 C CN1111604 C CN 1111604C
- Authority
- CN
- China
- Prior art keywords
- lactone
- pantoyl lactone
- enzyme
- substrate
- valerate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 102000004190 Enzymes Human genes 0.000 title claims abstract description 50
- 108090000790 Enzymes Proteins 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims abstract description 45
- 238000004519 manufacturing process Methods 0.000 title abstract description 11
- 229940070710 valerate Drugs 0.000 title abstract 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- 239000000758 substrate Substances 0.000 claims abstract description 22
- OTOIIPJYVQJATP-BYPYZUCNSA-N (R)-pantoic acid Chemical compound OCC(C)(C)[C@@H](O)C(O)=O OTOIIPJYVQJATP-BYPYZUCNSA-N 0.000 claims abstract description 20
- 230000002255 enzymatic effect Effects 0.000 claims abstract description 19
- 238000000855 fermentation Methods 0.000 claims abstract description 19
- 230000004151 fermentation Effects 0.000 claims abstract description 19
- 241000233732 Fusarium verticillioides Species 0.000 claims abstract description 8
- SERHXTVXHNVDKA-UHFFFAOYSA-N pantolactone Chemical compound CC1(C)COC(=O)C1O SERHXTVXHNVDKA-UHFFFAOYSA-N 0.000 claims description 45
- 244000005700 microbiome Species 0.000 claims description 15
- 230000001580 bacterial effect Effects 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 14
- 241000223218 Fusarium Species 0.000 claims description 10
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 230000001954 sterilising effect Effects 0.000 claims description 8
- 238000004659 sterilization and disinfection Methods 0.000 claims description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 235000010418 carrageenan Nutrition 0.000 claims description 6
- 229920001525 carrageenan Polymers 0.000 claims description 6
- 238000011081 inoculation Methods 0.000 claims description 5
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 238000012360 testing method Methods 0.000 claims description 4
- SERHXTVXHNVDKA-BYPYZUCNSA-N (R)-pantolactone Chemical compound CC1(C)COC(=O)[C@@H]1O SERHXTVXHNVDKA-BYPYZUCNSA-N 0.000 claims description 3
- 239000001888 Peptone Substances 0.000 claims description 3
- 108010080698 Peptones Proteins 0.000 claims description 3
- 240000008042 Zea mays Species 0.000 claims description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 3
- 229940041514 candida albicans extract Drugs 0.000 claims description 3
- 235000005822 corn Nutrition 0.000 claims description 3
- 238000006911 enzymatic reaction Methods 0.000 claims description 3
- 235000019319 peptone Nutrition 0.000 claims description 3
- 238000007670 refining Methods 0.000 claims description 3
- 239000012138 yeast extract Substances 0.000 claims description 3
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 239000002054 inoculum Substances 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 27
- 230000007062 hydrolysis Effects 0.000 abstract description 26
- 241000894006 Bacteria Species 0.000 abstract description 10
- 210000001822 immobilized cell Anatomy 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 6
- 239000003795 chemical substances by application Substances 0.000 abstract description 5
- 230000008569 process Effects 0.000 abstract description 5
- 238000007273 lactonization reaction Methods 0.000 abstract description 4
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 abstract description 3
- 230000007071 enzymatic hydrolysis Effects 0.000 abstract description 2
- 238000005457 optimization Methods 0.000 abstract 1
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 19
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 230000003287 optical effect Effects 0.000 description 12
- 108090000604 Hydrolases Proteins 0.000 description 11
- 102000004157 Hydrolases Human genes 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 235000019161 pantothenic acid Nutrition 0.000 description 10
- 239000011713 pantothenic acid Substances 0.000 description 10
- FRXSZNDVFUDTIR-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(OC)=CC=C21 FRXSZNDVFUDTIR-UHFFFAOYSA-N 0.000 description 9
- 230000000813 microbial effect Effects 0.000 description 9
- 229940055726 pantothenic acid Drugs 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- SERHXTVXHNVDKA-SCSAIBSYSA-N (3s)-3-hydroxy-4,4-dimethyloxolan-2-one Chemical compound CC1(C)COC(=O)[C@H]1O SERHXTVXHNVDKA-SCSAIBSYSA-N 0.000 description 8
- FAPWYRCQGJNNSJ-UBKPKTQASA-L calcium D-pantothenic acid Chemical compound [Ca+2].OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O.OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O FAPWYRCQGJNNSJ-UBKPKTQASA-L 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 235000004866 D-panthenol Nutrition 0.000 description 6
- 239000011703 D-panthenol Substances 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- OTOIIPJYVQJATP-UHFFFAOYSA-N pantoic acid Chemical compound OCC(C)(C)C(O)C(O)=O OTOIIPJYVQJATP-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- 229960003949 dexpanthenol Drugs 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- 235000019156 vitamin B Nutrition 0.000 description 4
- 239000011720 vitamin B Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- FAPWYRCQGJNNSJ-UHFFFAOYSA-L Calcium DL-pantothenate Chemical compound [Ca+2].OCC(C)(C)C(O)C(=O)NCCC([O-])=O.OCC(C)(C)C(O)C(=O)NCCC([O-])=O FAPWYRCQGJNNSJ-UHFFFAOYSA-L 0.000 description 3
- 229930191978 Gibberellin Natural products 0.000 description 3
- 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 3
- 102000018997 Growth Hormone Human genes 0.000 description 3
- 108010051696 Growth Hormone Proteins 0.000 description 3
- 206010024642 Listless Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 229940000635 beta-alanine Drugs 0.000 description 3
- -1 calcium salt D-calcium pantothenate Chemical class 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 description 3
- 239000003448 gibberellin Substances 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 239000000122 growth hormone Substances 0.000 description 3
- 231100000350 mutagenesis Toxicity 0.000 description 3
- 238000002703 mutagenesis Methods 0.000 description 3
- 231100000219 mutagenic Toxicity 0.000 description 3
- 230000003505 mutagenic effect Effects 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- 230000008635 plant growth Effects 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RGJOEKWQDUBAIZ-IBOSZNHHSA-N CoASH Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS)O[C@H]1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-IBOSZNHHSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 241001149959 Fusarium sp. Species 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- 229930003270 Vitamin B Natural products 0.000 description 2
- 235000010724 Wisteria floribunda Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229960002079 calcium pantothenate Drugs 0.000 description 2
- 159000000007 calcium salts Chemical group 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 description 2
- 239000005516 coenzyme A Substances 0.000 description 2
- 229940093530 coenzyme a Drugs 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000413 hydrolysate Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 210000005036 nerve Anatomy 0.000 description 2
- 230000035790 physiological processes and functions Effects 0.000 description 2
- 244000144977 poultry Species 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 230000006340 racemization Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 150000003722 vitamin derivatives Chemical class 0.000 description 2
- OTOIIPJYVQJATP-SCSAIBSYSA-N (2s)-2,4-dihydroxy-3,3-dimethylbutanoic acid Chemical compound OCC(C)(C)[C@H](O)C(O)=O OTOIIPJYVQJATP-SCSAIBSYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 241000723247 Cylindrocarpon Species 0.000 description 1
- 101000925662 Enterobacteria phage PRD1 Endolysin Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000223221 Fusarium oxysporum Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000896533 Gliocladium Species 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- ZNXZGRMVNNHPCA-UHFFFAOYSA-N Pantetheine Natural products OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS ZNXZGRMVNNHPCA-UHFFFAOYSA-N 0.000 description 1
- 206010054048 Postoperative ileus Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000007642 Vitamin B Deficiency Diseases 0.000 description 1
- 241001306237 Volutella Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical compound Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
- RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000007073 chemical hydrolysis Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000000058 esterolytic effect Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000012262 fermentative production Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 108010031620 mandelonitrile lyase Proteins 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- ZNXZGRMVNNHPCA-VIFPVBQESA-N pantetheine Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS ZNXZGRMVNNHPCA-VIFPVBQESA-N 0.000 description 1
- 229940101267 panthenol Drugs 0.000 description 1
- 229940014662 pantothenate Drugs 0.000 description 1
- 235000020957 pantothenol Nutrition 0.000 description 1
- 239000011619 pantothenol Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 244000000003 plant pathogen Species 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000004102 tricarboxylic acid cycle Effects 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 229940046001 vitamin b complex Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
Transform number of times | 1 | 2 | 3 | 4 | 5 | 6 |
Transformation efficiency (%) | 30.5 | 31.1 | 29.3 | 28.6 | 29.3 | 29.6 |
Transform number of times | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 |
Transformation efficiency (%) | 28.5 | 30.1 | 32.2 | 30.5 | 29.3 | 29.6 | 30.5 | 31.2 | 28.6 | 31.5 |
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 01104070 CN1111604C (en) | 2001-02-21 | 2001-02-21 | Process for preparing D-lactone valerate by microbe enzyme method |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 01104070 CN1111604C (en) | 2001-02-21 | 2001-02-21 | Process for preparing D-lactone valerate by microbe enzyme method |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1313402A CN1313402A (en) | 2001-09-19 |
CN1111604C true CN1111604C (en) | 2003-06-18 |
Family
ID=4653656
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 01104070 Expired - Lifetime CN1111604C (en) | 2001-02-21 | 2001-02-21 | Process for preparing D-lactone valerate by microbe enzyme method |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN1111604C (en) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1202982B1 (en) * | 1999-07-22 | 2003-11-26 | Firmenich Sa | Method for preparing a gamma-unsaturated beta-lactone and use thereof as an aromatic and flavouring ingredient |
CN100351369C (en) * | 2005-11-22 | 2007-11-28 | 浙江杭州鑫富药业股份有限公司 | Microorganism of producing D-pantothenic acid enternal ester hydrolase and process for preparing D-pantothenic acid thereof |
CN1935977B (en) * | 2006-10-19 | 2010-06-09 | 华东理工大学 | Levo lactone hydrolase producing fungus, and its method for preparing chiral hydroxy acid |
CN116217427A (en) * | 2018-01-10 | 2023-06-06 | 精晶药业股份有限公司 | Preparation method of D-calcium pantothenate |
CN108117532A (en) * | 2018-01-12 | 2018-06-05 | 重庆市碚圣医药科技股份有限公司 | A kind of synthetic method of the D-VB5 lactone of high-purity |
CN108192884B (en) * | 2018-01-16 | 2021-11-19 | 重庆市碚圣医药科技股份有限公司 | D-pantoic acid lactone hydrolase fermentation and cell immobilization method |
CN108624513B (en) * | 2018-06-15 | 2020-11-03 | 成都本则生科技有限公司 | Method for high-density culture of D-pantolactone hydrolase producing strain and application |
CN110157623B (en) * | 2018-12-21 | 2022-07-12 | 合肥工业大学 | Fusarium strain and method for producing D-pantolactone hydrolase by fermenting same |
CN111621541A (en) | 2019-02-27 | 2020-09-04 | 上海艾美晶生物科技有限公司 | Method for resolving optical isomers using electrodialysis techniques |
CN110004135A (en) * | 2019-03-18 | 2019-07-12 | 合肥华恒生物工程有限公司 | A kind of method of ball shape fixation hydrolase containing D-pantoyl lactone cell and preparation method thereof and hydrolysis D-pantoyl lactone |
CN111850081B (en) | 2019-04-26 | 2022-03-01 | 广安摩珈生物科技有限公司 | Method for resolving optical isomers using supercritical fluid extraction techniques |
CN110845453A (en) * | 2019-11-28 | 2020-02-28 | 安徽泰格生物科技有限公司 | Racemization method of L-pantoic acid lactone |
CN111117897B (en) * | 2019-12-30 | 2022-07-08 | 常州悦朋科技有限公司 | Fusarium moniliforme JHpharm 2-1 for high-yield D-pantolactone hydrolase and fermentation method thereof |
CN112028758B (en) * | 2020-05-25 | 2024-09-10 | 广安摩珈生物科技有限公司 | Process for preparing hydroxyaldehydes and process for resolution of optical isomers using electrodialysis technique |
CN112481345A (en) * | 2020-12-18 | 2021-03-12 | 合肥工业大学 | Method for preparing D-pantoic acid by continuous catalysis |
-
2001
- 2001-02-21 CN CN 01104070 patent/CN1111604C/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
CN1313402A (en) | 2001-09-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101392278B (en) | Method for preparing D-pantolactone by microbe mixed fermentation method | |
CN1111604C (en) | Process for preparing D-lactone valerate by microbe enzyme method | |
CN105950679B (en) | Method for preparing D-pantolactone by fermentation | |
CN1935977B (en) | Levo lactone hydrolase producing fungus, and its method for preparing chiral hydroxy acid | |
CN1516737A (en) | Process for preparation of gallic acid by co-culture | |
CN101701246B (en) | Method for screening high-yield D-pantolactone hydrolytic enzyme strain | |
CN101134943B (en) | Bacillus alcaligenes and method for preparing single enantiomer amygdalic acid | |
CN1165610C (en) | Aspergillus niger and its microbial conversion process of producing vanillic acid and vanillic aldehyde | |
CN101701243B (en) | Method for producing R-mandelic acid and derivates thereof by biocatalysis | |
CN1724646A (en) | Bacillus subtilis mutant strain, breeding method and application in fermentation method of producing adenosin | |
CN101250492B (en) | Agrobacterium strain and method for preparing left-lateral lactone compounds thereby | |
CN1164737C (en) | Preparation of gamma-polyglutamic acid and its salt and glutathione and its precursor by using Bacillus subtilis NX-2 | |
CN1229490C (en) | 'Tabin' aspergillus capable of producing pectase in high yield, and application in production of solid-state fermentation | |
CN1173042C (en) | Method for preparing D-pantothenic alcohol by using microbial enzyme method | |
CN110205345B (en) | Method for producing gamma-aminobutyric acid by using red yeast rice fermented yellow wine processing byproducts | |
CN108410749A (en) | The method that marine low temperature (+) gamma-lactam enzyme asymmetric hydrolysis prepares (-) gamma-lactam | |
CN1827771A (en) | Microorganism polysaccharide and its preparation method and application | |
CN102851238A (en) | Sphingobacterium and method for preparing levetiracetam acid by utilizing same | |
CN1778889A (en) | Biological catalytic preparation of (S)-4-chlorine-3-hydroxy-butanoic acid ester and bacterium therewith | |
CN87100655A (en) | Method for producing L-sorbose | |
CN1292064C (en) | Microorganism strain and method for converting cephalosporin C into deacetylate cephalosporin C by using same | |
CN1648242A (en) | Permeable cell trehalose synthease and its preparation and use | |
CN101078019A (en) | Method for producing coenzyme Q10 by enzyme engineering method | |
CN1077600C (en) | Epherdrine producing method by using large-scale ephedra cell culture as material | |
CN105176954B (en) | A kind of method that arginine deiminase is prepared using bacterial strain MQO-153 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C06 | Publication | ||
PB01 | Publication | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C56 | Change in the name or address of the patentee |
Owner name: ZHEJIANG HANGZHOU XINFU PHARMACEUTICAL CO., LTD. Free format text: FORMER NAME OR ADDRESS: XINFU BIO-CHEMICAL CO LTD, ZHEJIANG |
|
CP03 | Change of name, title or address |
Address after: 311301 Ling'an Economic Development Zone, Zhejiang Patentee after: ZHEJIANG HANGZHOU XINFU PHARMACEUTICAL Co.,Ltd. Address before: 311301 Jin Town, Hangzhou City, Zhejiang, Ling'an Patentee before: Zhejiang Xinfu Biological Chemical Co.,Ltd. |
|
C41 | Transfer of patent application or patent right or utility model | ||
C56 | Change in the name or address of the patentee | ||
CP01 | Change in the name or title of a patent holder |
Address after: 311301 Ling'an Economic Development Zone, Zhejiang Patentee after: YIFAN XINFU PHARMACEUTICAL Co.,Ltd. Address before: 311301 Ling'an Economic Development Zone, Zhejiang Patentee before: ZHEJIANG HANGZHOU XINFU PHARMACEUTICAL Co.,Ltd. |
|
TR01 | Transfer of patent right |
Effective date of registration: 20160623 Address after: Hangzhou City, Zhejiang province 311300 Ling'an City Kam South Street No. 9 Gua fan Patentee after: HANGZHOU XINFU SCIENCE & TECHNOLOGY Co.,Ltd. Address before: 311301 Ling'an Economic Development Zone, Zhejiang Patentee before: YIFAN XINFU PHARMACEUTICAL Co.,Ltd. |
|
CX01 | Expiry of patent term |
Granted publication date: 20030618 |
|
CX01 | Expiry of patent term |