CA1132922A - Obtention d'epoxyde par des microorganismes immobilises dans une matrice - Google Patents

Obtention d'epoxyde par des microorganismes immobilises dans une matrice

Info

Publication number: CA1132922A
Authority: CA; Canada
Prior art keywords: microorganism; epoxide; cells; immobilized cells; medium
Prior art date: 1978-08-11
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

Application number

CA333,011A

Other languages

English (en)

Inventor

Seiichi Uchida

Keizo Furuhashi

Akira Taoka

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bio Research Center Co Ltd

Original Assignee

Bio Research Center Co Ltd

Priority date (The priority date 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 date listed.)

1978-08-11

Filing date

1979-08-01

Publication date

1982-10-05

1979-08-01 Application filed by Bio Research Center Co Ltd filed Critical Bio Research Center Co Ltd

1982-10-05 Application granted granted Critical

1982-10-05 Publication of CA1132922A publication Critical patent/CA1132922A/fr

Status Expired legal-status Critical Current

Links

210000001822 immobilized cell Anatomy 0.000 title claims description 38
238000004519 manufacturing process Methods 0.000 title claims description 8
150000002118 epoxides Chemical class 0.000 title claims 6
244000005700 microbiome Species 0.000 claims abstract description 51
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 13
239000012736 aqueous medium Substances 0.000 claims abstract description 10
230000000379 polymerizing effect Effects 0.000 claims abstract description 6
239000002609 medium Substances 0.000 claims description 36
238000006243 chemical reaction Methods 0.000 claims description 32
238000000034 method Methods 0.000 claims description 30
210000004027 cell Anatomy 0.000 claims description 28
235000015097 nutrients Nutrition 0.000 claims description 18
230000008569 process Effects 0.000 claims description 12
ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 10
239000000178 monomer Substances 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 7
229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 7
241001509401 Gordonia rubripertincta Species 0.000 claims description 5
238000003306 harvesting Methods 0.000 claims description 3
230000006872 improvement Effects 0.000 claims description 3
238000006116 polymerization reaction Methods 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
238000012258 culturing Methods 0.000 claims description 2
239000004593 Epoxy Substances 0.000 claims 1
150000001335 aliphatic alkanes Chemical class 0.000 claims 1
238000010348 incorporation Methods 0.000 abstract 1
150000002430 hydrocarbons Chemical class 0.000 description 21
229930195733 hydrocarbon Natural products 0.000 description 20
150000002924 oxiranes Chemical class 0.000 description 19
239000008363 phosphate buffer Substances 0.000 description 15
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 14
238000012360 testing method Methods 0.000 description 13
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
230000000694 effects Effects 0.000 description 11
239000007789 gas Substances 0.000 description 11
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 11
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 11
241000187654 Nocardia Species 0.000 description 10
239000004215 Carbon black (E152) Substances 0.000 description 9
239000000243 solution Substances 0.000 description 9
241000187561 Rhodococcus erythropolis Species 0.000 description 8
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
239000006916 nutrient agar Substances 0.000 description 8
239000001301 oxygen Substances 0.000 description 8
229910052760 oxygen Inorganic materials 0.000 description 8
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 7
239000008103 glucose Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
241000186216 Corynebacterium Species 0.000 description 6
229910002651 NO3 Inorganic materials 0.000 description 6
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 6
229940117913 acrylamide Drugs 0.000 description 6
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 6
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 6
230000009467 reduction Effects 0.000 description 6
235000000346 sugar Nutrition 0.000 description 6
150000008163 sugars Chemical class 0.000 description 6
241000186146 Brevibacterium Species 0.000 description 5
102000016938 Catalase Human genes 0.000 description 5
108010053835 Catalase Proteins 0.000 description 5
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 5
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 5
WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 5
229930091371 Fructose Natural products 0.000 description 5
239000005715 Fructose Substances 0.000 description 5
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 5
239000001828 Gelatine Substances 0.000 description 5
229920002472 Starch Polymers 0.000 description 5
229930006000 Sucrose Natural products 0.000 description 5
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 5
108010046334 Urease Proteins 0.000 description 5
229920000159 gelatin Polymers 0.000 description 5
235000019322 gelatine Nutrition 0.000 description 5
238000009630 liquid culture Methods 0.000 description 5
235000013336 milk Nutrition 0.000 description 5
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238000000926 separation method Methods 0.000 description 5
239000000600 sorbitol Substances 0.000 description 5
238000009633 stab culture Methods 0.000 description 5
239000008107 starch Substances 0.000 description 5
235000019698 starch Nutrition 0.000 description 5
239000000758 substrate Substances 0.000 description 5
239000005720 sucrose Substances 0.000 description 5
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 4
SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
229930195725 Mannitol Natural products 0.000 description 4
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 4
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 4
239000004202 carbamide Substances 0.000 description 4
230000008859 change Effects 0.000 description 4
239000010432 diamond Substances 0.000 description 4
238000004817 gas chromatography Methods 0.000 description 4
238000007429 general method Methods 0.000 description 4
239000001963 growth medium Substances 0.000 description 4
229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
239000000594 mannitol Substances 0.000 description 4
235000010355 mannitol Nutrition 0.000 description 4
239000012528 membrane Substances 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
239000000725 suspension Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
235000014653 Carica parviflora Nutrition 0.000 description 3
241000243321 Cnidaria Species 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
238000010908 decantation Methods 0.000 description 3
239000008367 deionised water Substances 0.000 description 3
229910021641 deionized water Inorganic materials 0.000 description 3
-1 ethylene, propylene Chemical group 0.000 description 3
238000013467 fragmentation Methods 0.000 description 3
238000006062 fragmentation reaction Methods 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
235000002639 sodium chloride Nutrition 0.000 description 3
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 2
239000006285 cell suspension Substances 0.000 description 2
239000013043 chemical agent Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000011109 contamination Methods 0.000 description 2
JEJVUMPKJVMOEZ-UHFFFAOYSA-N hexadeca-1,15-diene Chemical compound C=CCCCCCCCCCCCCC=C JEJVUMPKJVMOEZ-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000011282 treatment Methods 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
PKXHXOTZMFCXSH-UHFFFAOYSA-N 3,3-dimethylbut-1-ene Chemical compound CC(C)(C)C=C PKXHXOTZMFCXSH-UHFFFAOYSA-N 0.000 description 1
RDQHPQAJTZBSFV-UHFFFAOYSA-N 4-ethyl-3,4-dimethylhex-1-ene Chemical compound CCC(C)(CC)C(C)C=C RDQHPQAJTZBSFV-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
239000004254 Ammonium phosphate Substances 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
241000595586 Coryne Species 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
239000011837 N,N-methylenebisacrylamide Substances 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000001888 Peptone Substances 0.000 description 1
108010080698 Peptones Proteins 0.000 description 1
MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 1
150000003926 acrylamides Chemical class 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000008272 agar Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
229910001870 ammonium persulfate Inorganic materials 0.000 description 1
229910000148 ammonium phosphate Inorganic materials 0.000 description 1
235000019289 ammonium phosphates Nutrition 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
230000000721 bacterilogical effect Effects 0.000 description 1
235000015278 beef Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
229940041514 candida albicans extract Drugs 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000002844 continuous effect Effects 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
239000002360 explosive Substances 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000011790 ferrous sulphate Substances 0.000 description 1
235000003891 ferrous sulphate Nutrition 0.000 description 1
229930182830 galactose Natural products 0.000 description 1
230000003100 immobilizing effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
229960000367 inositol Drugs 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
229940099596 manganese sulfate Drugs 0.000 description 1
239000011702 manganese sulphate Substances 0.000 description 1
235000007079 manganese sulphate Nutrition 0.000 description 1
SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
239000003973 paint Substances 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
238000005070 sampling Methods 0.000 description 1
CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
235000011008 sodium phosphates Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000004753 textile Substances 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/14—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Zoology (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
Microbiology (AREA)
General Chemical & Material Sciences (AREA)
Biotechnology (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Immobilizing And Processing Of Enzymes And Microorganisms (AREA)

CA333,011A 1978-08-11 1979-08-01 Obtention d'epoxyde par des microorganismes immobilises dans une matrice Expired CA1132922A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP9808178A JPS5526806A (en)	1978-08-11	1978-08-11	Preparation of epoxides by immobilized microorganism
JP53/98081		1978-08-11

Publications (1)

Publication Number	Publication Date
CA1132922A true CA1132922A (fr)	1982-10-05

Family

ID=14210386

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA333,011A Expired CA1132922A (fr)	1978-08-11	1979-08-01	Obtention d'epoxyde par des microorganismes immobilises dans une matrice

Country Status (6)

Country	Link
JP (1)	JPS5526806A (fr)
BE (1)	BE878201A (fr)
CA (1)	CA1132922A (fr)
DE (1)	DE2931148A1 (fr)
FR (1)	FR2433047A1 (fr)
GB (1)	GB2028315B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS572692A (en) *	1980-06-04	1982-01-08	Baiorisaac Center:Kk	Preparation of volatile epoxide by microorganism
CA1240942A (fr) *	1984-05-28	1988-08-23	Keizo Furuhashi	Preparation d'epoxydes a l'aide de micro-organismes

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2306213A1 (fr) *	1975-04-04	1976-10-29	Rhone Poulenc Ind	Enzymes immobilisees
US4102744A (en) *	1976-12-20	1978-07-25	Exxon Research & Engineering Co.	Two phase fermentation
JPS5411297A (en) *	1977-06-24	1979-01-27	Bio Research Center Co	Production of epoxides by microorganism
DK154779A (da) *	1978-04-14	1979-10-15	Exxon Research Engineering Co	Fremgangsmaade til epoxidation af lavere alfaolefiner

1978
- 1978-08-11 JP JP9808178A patent/JPS5526806A/ja active Granted
1979
- 1979-07-24 GB GB7925793A patent/GB2028315B/en not_active Expired
- 1979-08-01 CA CA333,011A patent/CA1132922A/fr not_active Expired
- 1979-08-01 DE DE19792931148 patent/DE2931148A1/de not_active Ceased
- 1979-08-10 FR FR7920511A patent/FR2433047A1/fr active Granted
- 1979-08-10 BE BE0/196698A patent/BE878201A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
FR2433047A1 (fr)	1980-03-07
FR2433047B1 (fr)	1983-12-16
DE2931148A1 (de)	1980-03-06
GB2028315B (en)	1982-10-13
JPS5526806A (en)	1980-02-26
GB2028315A (en)	1980-03-05
JPS5646790B2 (fr)	1981-11-05
BE878201A (fr)	1980-02-11

Legal Events

Date	Code	Title	Description
1999-10-05	MKEX	Expiry

Publication	Publication Date	Title
Gottschal et al.	1981	Non-production of acetone and butanol by Clostridium acetobutylicum during glucose-and ammonium-limitation in continuous culture
JPS61162193A (ja)	1986-07-22	微生物によるアミド類の製造法
US4347320A (en)	1982-08-31	Immobilization of microorganisms in gelled carrageenan
US4384044A (en)	1983-05-17	Production of microbial polysaccharides
EP0146329A2 (fr)	1985-06-26	Procédé de préparation de supports polymériques contenant des oxiranes pour l'immobilisation d'enzymes et autres matériaux contenant de l'hydrogène actif, et supports polymériques contenant des oxiranes
Haight et al.	1962	Interaction between the parameters of hydrostatic pressure and temperature on aspartase of Escherichia coli
Chibata et al.	1986	Continuous production of L-aspartic acid: Improvement of productivity by both development of immobilization method and construction of new Escherichia coli strain
CA1132922A (fr)	1982-10-05	Obtention d'epoxyde par des microorganismes immobilises dans une matrice
JPS6291189A (ja)	1987-04-25	アミドの微生物学的製造法
US4696901A (en)	1987-09-29	Immobilization of microorganisms on a plastic carrier
US4081327A (en)	1978-03-28	Preparation of d-fructose
US4343899A (en)	1982-08-10	Process for producing stable aqueous solution of acrylamide or methacrylamide
Lee et al.	1989	Biosynthesis of acrylamide from acrylonitrile in aqueous two phase system
US4612288A (en)	1986-09-16	Oxirane resins for enzyme immobilization
JPH0155879B2 (fr)	1989-11-28
FR2471409A1 (fr)	1981-06-19	Procede de preparation du glucoside de l'acide mycophenolique, et glucoside ainsi obtenu
SU671738A3 (ru)	1979-06-30	Способ получени биомассы микроорганизмов
Hanzlíkova et al.	1984	Formation of poly-3-hydroxybutyrate by a soil microbial community during batch and heterocontinuous cultivation
KR900006999B1 (ko)	1990-09-25	아크릴아마이드의 생물학적 제조방법
GB2082189A (en)	1982-03-03	Production of microbial polysaccharides
KR910007850B1 (ko)	1991-10-02	고농도 아크릴로니트릴로부터의 아크릴아마이드의 제조 방법 및 이에 이용되는 미생물
Linton et al.	1980	Growth of an Ethane‐utilizing Mixed Culture in a Chemostat
SU1551743A1 (ru)	1990-03-23	Способ получени левана
SU1157057A1 (ru)	1985-05-23	Способ получени протеолитического фермента
JPS6147194A (ja)	1986-03-07	Ｎ−カルバモイル−ｄ−バリンまたはｄ−バリンの製造法