JPH01148193A - Production of 5-aminolevulic acid - Google Patents
Production of 5-aminolevulic acidInfo
- Publication number
- JPH01148193A JPH01148193A JP30694087A JP30694087A JPH01148193A JP H01148193 A JPH01148193 A JP H01148193A JP 30694087 A JP30694087 A JP 30694087A JP 30694087 A JP30694087 A JP 30694087A JP H01148193 A JPH01148193 A JP H01148193A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- ala
- culture
- methanosarcina
- strain
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 239000002253 acid Substances 0.000 title abstract description 8
- 244000005700 microbiome Species 0.000 claims abstract description 11
- 241000205276 Methanosarcina Species 0.000 claims abstract description 7
- 238000012258 culturing Methods 0.000 claims abstract description 7
- ZGXJTSGNIOSYLO-UHFFFAOYSA-N 88755TAZ87 Chemical compound NCC(=O)CCC(O)=O ZGXJTSGNIOSYLO-UHFFFAOYSA-N 0.000 claims description 28
- 229960002749 aminolevulinic acid Drugs 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 8
- 241000134675 Methanosarcina barkeri str. Fusaro Species 0.000 abstract description 5
- 239000001963 growth medium Substances 0.000 abstract description 5
- 239000002609 medium Substances 0.000 abstract description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract description 4
- 229910052799 carbon Inorganic materials 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 4
- 239000002243 precursor Substances 0.000 abstract description 3
- 239000006228 supernatant Substances 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 235000019270 ammonium chloride Nutrition 0.000 abstract description 2
- 239000011780 sodium chloride Substances 0.000 abstract description 2
- 239000001384 succinic acid Substances 0.000 abstract description 2
- WYEPBHZLDUPIOD-UHFFFAOYSA-N 4,6-dioxoheptanoic acid Chemical compound CC(=O)CC(=O)CCC(O)=O WYEPBHZLDUPIOD-UHFFFAOYSA-N 0.000 abstract 1
- -1 NaCl Chemical class 0.000 abstract 1
- 238000010828 elution Methods 0.000 abstract 1
- 238000005342 ion exchange Methods 0.000 abstract 1
- 231100000219 mutagenic Toxicity 0.000 abstract 1
- 230000003505 mutagenic effect Effects 0.000 abstract 1
- 239000004575 stone Substances 0.000 abstract 1
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 229940040102 levulinic acid Drugs 0.000 description 6
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 5
- 230000001580 bacterial effect Effects 0.000 description 5
- 239000007640 basal medium Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 4
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 4
- 235000002639 sodium chloride Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- 229940088594 vitamin Drugs 0.000 description 3
- 235000013343 vitamin Nutrition 0.000 description 3
- 239000011782 vitamin Substances 0.000 description 3
- 229930003231 vitamin Natural products 0.000 description 3
- 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 2
- MSYNCHLYGJCFFY-UHFFFAOYSA-B 2-hydroxypropane-1,2,3-tricarboxylate;titanium(4+) Chemical compound [Ti+4].[Ti+4].[Ti+4].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O MSYNCHLYGJCFFY-UHFFFAOYSA-B 0.000 description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 102000004867 Hydro-Lyases Human genes 0.000 description 2
- 108090001042 Hydro-Lyases Proteins 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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- HWXBTNAVRSUOJR-UHFFFAOYSA-N alpha-hydroxyglutaric acid Natural products OC(=O)C(O)CCC(O)=O HWXBTNAVRSUOJR-UHFFFAOYSA-N 0.000 description 2
- 229940009533 alpha-ketoglutaric acid Drugs 0.000 description 2
- 229960004050 aminobenzoic acid Drugs 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229960002685 biotin Drugs 0.000 description 2
- 235000020958 biotin Nutrition 0.000 description 2
- 239000011616 biotin Substances 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 229960000304 folic acid Drugs 0.000 description 2
- 235000019152 folic acid Nutrition 0.000 description 2
- 239000011724 folic acid Substances 0.000 description 2
- 235000013922 glutamic acid Nutrition 0.000 description 2
- 239000004220 glutamic acid Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 229960003512 nicotinic acid Drugs 0.000 description 2
- 235000001968 nicotinic acid Nutrition 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000011573 trace mineral Substances 0.000 description 2
- 235000013619 trace mineral Nutrition 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
- 150000003722 vitamin derivatives Chemical class 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 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
- PWKSKIMOESPYIA-UHFFFAOYSA-N 2-acetamido-3-sulfanylpropanoic acid Chemical compound CC(=O)NC(CS)C(O)=O PWKSKIMOESPYIA-UHFFFAOYSA-N 0.000 description 1
- NNMALANKTSRILL-LXENMSTPSA-N 3-[(2z,5e)-2-[[3-(2-carboxyethyl)-5-[(z)-[(3e,4r)-3-ethylidene-4-methyl-5-oxopyrrolidin-2-ylidene]methyl]-4-methyl-1h-pyrrol-2-yl]methylidene]-5-[(4-ethyl-3-methyl-5-oxopyrrol-2-yl)methylidene]-4-methylpyrrol-3-yl]propanoic acid Chemical compound O=C1C(CC)=C(C)C(\C=C\2C(=C(CCC(O)=O)C(=C/C3=C(C(C)=C(\C=C/4\C(\[C@@H](C)C(=O)N\4)=C\C)N3)CCC(O)=O)/N/2)C)=N1 NNMALANKTSRILL-LXENMSTPSA-N 0.000 description 1
- PMYDPQQPEAYXKD-UHFFFAOYSA-N 3-hydroxy-n-naphthalen-2-ylnaphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(NC(=O)C3=CC4=CC=CC=C4C=C3O)=CC=C21 PMYDPQQPEAYXKD-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
- 241000195628 Chlorophyta Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- 229940123274 Dehydratase inhibitor Drugs 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000202974 Methanobacterium Species 0.000 description 1
- 241000205275 Methanosarcina barkeri Species 0.000 description 1
- 241001302042 Methanothermobacter thermautotrophicus Species 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- WFWLQNSHRPWKFK-UHFFFAOYSA-N Tegafur Chemical compound O=C1NC(=O)C(F)=CN1C1OCCC1 WFWLQNSHRPWKFK-UHFFFAOYSA-N 0.000 description 1
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
- 229930003270 Vitamin B Natural products 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 229960003767 alanine Drugs 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
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 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 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229960002713 calcium chloride Drugs 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229960002079 calcium pantothenate Drugs 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000012136 culture method 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
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 229960001781 ferrous sulfate Drugs 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000004095 hydrolyase inhibitor Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 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
- AGBQKNBQESQNJD-UHFFFAOYSA-M lipoate Chemical compound [O-]C(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-M 0.000 description 1
- 235000019136 lipoic acid Nutrition 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- 229940099607 manganese chloride Drugs 0.000 description 1
- 239000013028 medium composition Substances 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000243 photosynthetic effect Effects 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 229960002668 sodium chloride Drugs 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000011655 sodium selenate Substances 0.000 description 1
- 235000018716 sodium selenate Nutrition 0.000 description 1
- 229960001881 sodium selenate Drugs 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Abstract
Description
【発明の詳細な説明】
(産業上の利用分野)
本発明は、メタノサルシナ属に属する微生物の培養によ
る、5−アミノレブリン酸(以下、5−ALAと略記す
る)の製造法に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a method for producing 5-aminolevulinic acid (hereinafter abbreviated as 5-ALA) by culturing a microorganism belonging to the genus Methanosarcina.
5−ALAは、植物ホルモンの一種で、農薬として注目
されている化合物であり、また、クロロフィル、ビタミ
ンB12.フィコビリン、ファクタ’ 430等のテト
ラビロール化合物の前駆体としても知られている。5-ALA is a type of plant hormone and a compound that is attracting attention as an agricultural chemical.It is also a compound that is attracting attention as a pesticide. It is also known as a precursor of tetravirol compounds such as phycobilin and Factor' 430.
(従来技術)
従来、微生物を用いて5−ALAを製造する方法として
、メタノバクテリウム サーモオートド074カム(M
ethanobacterium thermoaut
otr。(Prior Art) Conventionally, as a method for producing 5-ALA using microorganisms, Methanobacterium thermoautod074cam (M
ethanobacterium thermoout
otr.
phtcum)を用いる方法が知られている(アーカイ
ブズ オブ ミクロバイオロジー(A rch、 M
icr。phtcum) is known (Archives of Microbiology (Arch, M.
icr.
biol、)、 135 、237〜240.(198
3))、 また、5−ALAの生成に関する代謝経路に
ついても種々の検討がされており、動物、酵母。biol, ), 135, 237-240. (198
3)) Various studies have also been conducted on the metabolic pathways related to the production of 5-ALA, including animals and yeast.
光合成細菌を含む細菌などではサクシニル−C。Succinyl-C in bacteria including photosynthetic bacteria.
Aとグリシンから合成されるシェミン経路、高等植物、
緑藻などではコハク酸からα−ケトグルタル酸を経由す
るC−5経路が知られている。C−5経路の中間体とし
てはグルタミン酸あるいは4゜5−ジオキシ吉草酸が想
定されているが、酵素学的な証明は未だなされていない
。Shemin pathway synthesized from A and glycine, higher plants,
In green algae, the C-5 pathway from succinic acid to α-ketoglutaric acid is known. Glutamic acid or 4.5-dioxyvaleric acid is assumed to be an intermediate in the C-5 pathway, but enzymatic proof has not yet been provided.
(発明が解決しようとする問題点)
メタノバクテリウム サーモオートトロフィカムの培養
によって5−ALAを製造する方法は、炭素源およびエ
ネルギー源として炭酸ガス、水素を用いる必要があり、
更に5−ALAを蓄積させるためには5−ALAの脱水
酵素である5−ALAデヒドラターゼを阻害するレブリ
ン酸を高濃度に添加しなくてはならず、経済的に有利な
方法でない。(Problems to be Solved by the Invention) The method for producing 5-ALA by culturing Methanobacterium thermoautotrophicum requires the use of carbon dioxide gas and hydrogen as a carbon source and an energy source.
In order to further accumulate 5-ALA, it is necessary to add a high concentration of levulinic acid, which inhibits 5-ALA dehydratase, which is a 5-ALA dehydratase, and this is not an economically advantageous method.
(問題を解決するための手段)
本発明者らは、5−ALAを生産する能力を有する微生
物を得ることを目的に自然界および公知の保存菌株につ
いて鋭意研究した結果、メタノサルシナ属に属する微生
物が5−ALAを培地中に多量に蓄積することを見出だ
し、本発明に至った。(Means for Solving the Problem) The present inventors conducted intensive research on natural and known preserved bacterial strains with the aim of obtaining microorganisms capable of producing 5-ALA. - It was discovered that ALA accumulates in large amounts in the culture medium, leading to the present invention.
すなわち、本発明は、メタノサルシナ属に属し、5−ア
ミノレブリン酸を生産する能力を有する微生物を培養し
、5−アミノレブリン酸を生成させ、これを採取するこ
とを特徴とする5−アミノレブリン酸の製造法である。That is, the present invention provides a method for producing 5-aminolevulinic acid, which comprises culturing a microorganism belonging to the genus Methanosarcina and having the ability to produce 5-aminolevulinic acid, producing 5-aminolevulinic acid, and collecting the same. It is.
本発明に使用される微生物は、メタノサルシナ属に属し
、5−ALAを生産する能力を有する微生物であれば、
野生株、変異株、 IMIIIIM合あるいは遺伝子組
み換えその他の遺伝的手法によって得られる株のいずれ
のものでもよい、その−例として、D S M (D
eutsche S amalung van M i
kroorganismen’)より入手可能なメタノ
サルシナ バーケリ(M ethanosarcina
barkeri ) D S M 804を挙げるこ
とができる0本菌の菌学的性質は、BerQe’l’S
1lantlal of determinativ
e baCt4)riol。The microorganism used in the present invention belongs to the genus Methanosarcina and has the ability to produce 5-ALA.
The strain may be a wild strain, a mutant strain, a strain obtained by IMIIIM hybridization, genetic recombination, or other genetic methods; for example, DSM (D
eutsche S amalung van M i
Methanosarcina barkeri available from
Berqe'l'S
1 lantlal of determinative
e baCt4)riol.
gV第8版に記載されている。gV 8th edition.
本発明に使用される培地は、炭素源、窒素源。The culture medium used in the present invention contains a carbon source and a nitrogen source.
イオウ源、無機塩、更に必要に応じて他の栄養素。Sulfur sources, inorganic salts, and other nutrients as needed.
微量要素等を添加して、嫌気的雰囲気にした培地が使用
される。A medium containing trace elements and the like to create an anaerobic atmosphere is used.
炭素源としては、メタノール、炭酸ガス、酢酸。Carbon sources include methanol, carbon dioxide, and acetic acid.
メチルアミン等が使用されるが、メタノールが特に好ま
しく、その濃度は2vハ%以下が好ましい。Methylamine and the like are used, but methanol is particularly preferred, and its concentration is preferably 2% or less.
メタノール濃度が高まると微生物の生育を阻害するので
、培養中のメタノール濃度を0.05〜1%に維持し、
逐次メタノールを添加し培養することもできる。As methanol concentration increases, it inhibits the growth of microorganisms, so maintain the methanol concentration during culture at 0.05 to 1%.
Cultivation can also be carried out by sequentially adding methanol.
窒素源としては、通常の微生物の培養に用いられる硫酸
アンモニウム、塩化アンモニウム、リン酸アンモニウム
、尿素、硝酸アンモニウム、硝酸ナトリウム等が挙げら
れる。Examples of the nitrogen source include ammonium sulfate, ammonium chloride, ammonium phosphate, urea, ammonium nitrate, and sodium nitrate, which are commonly used for culturing microorganisms.
無機塩としては、リン酸カリウム、硫酸マグネシウム、
塩化ナトリウム、塩化カルシウム、硫酸第一鉄、セレン
酸ナトリウム、塩化マンガンなどのほか、亜鉛、ホウ酸
、銅、ニッケル、モリブデンなどの添加も有効である。Inorganic salts include potassium phosphate, magnesium sulfate,
In addition to sodium chloride, calcium chloride, ferrous sulfate, sodium selenate, manganese chloride, etc., additions of zinc, boric acid, copper, nickel, molybdenum, etc. are also effective.
微量要素としては、ビオチン、葉酸、ビタミンB 、
B SB6.ニコチン酸、パントテン酸。Trace elements include biotin, folic acid, vitamin B,
BSB6. Nicotinic acid, pantothenic acid.
p−アミノ安息香酸、リボ酸などのビタミン類が用いら
れるほか、天然の栄養源としてコーン・ステイープ・リ
カー、酵母エキス、ペプトン等も添加できる。In addition to vitamins such as p-aminobenzoic acid and ribic acid, corn staple liquor, yeast extract, peptone, etc. can also be added as natural nutritional sources.
更に、5−ALAの前駆体として考えられるコハク酸、
α−ケトグルタル酸、グルタミン酸、4゜5−ジオキシ
吉草酸や、5−ALAデヒドラターゼ阻害剤であるレブ
リン酸などの添加により、5−ALAの生成量を増加さ
せることができる。Furthermore, succinic acid, which is considered as a precursor of 5-ALA,
The amount of 5-ALA produced can be increased by adding α-ketoglutaric acid, glutamic acid, 4°5-dioxyvaleric acid, or levulinic acid, which is a 5-ALA dehydratase inhibitor.
また、4,6−シケトヘブタン酸の添加によって5−A
LAの生成量を著しく高めることが可能である。この4
,6−シケトヘブタン酸は、1〜5mM程度の低濃度で
有効である。In addition, 5-A
It is possible to significantly increase the amount of LA produced. This 4
,6-siketohebutanoic acid is effective at concentrations as low as 1-5mM.
本発明における培養は、嫌気的に行なう必要がある。培
養を嫌気的に行なうには、培地中にL−システィン、チ
オ硫酸ナトリウム、クエン酸チタニウムなどの還元剤を
加えるほか、酸素を除去した窒素ガスや炭酸ガス、ある
いはこれらの混合気体を培地中に通気し、更に培養容器
の気相中に酸素が混入しないようにする方法が可能であ
る。Cultivation in the present invention must be performed anaerobically. To perform the culture anaerobically, in addition to adding a reducing agent such as L-cysteine, sodium thiosulfate, or titanium citrate to the medium, nitrogen gas from which oxygen has been removed, carbon dioxide gas, or a mixture of these gases is added to the medium. It is possible to provide aeration and also to prevent oxygen from being mixed into the gas phase of the culture container.
培養の形式としては、回分培養法でもよいが、生産の効
率化のためには担体に菌体な固定させ、培地を連続的に
供給する方法が好ましい、固定化に用いる担体としては
、微生物が付着できる多孔性の担体であればいかなる種
類のものでも用いることが可能であるが、具体的には、
発泡煉石、シリカ多孔質が挙げられる。Batch culture may be used as the culture method, but in order to improve production efficiency, it is preferable to immobilize the microorganisms on a carrier and continuously supply the culture medium. Any type of porous carrier that can be attached can be used, but specifically,
Examples include foamed brick and porous silica.
培養温度は25〜50℃で行なうが、30〜37℃が好
ましい、培!IpHは5.8〜7.O1好ましくは6.
3〜6.8に調節する。培養は通常3〜8日で終了する
が、他の培養条件に応じて適当に変えることができる。The culture temperature is 25 to 50°C, preferably 30 to 37°C. IpH is 5.8-7. O1 preferably 6.
Adjust to 3-6.8. Culture usually ends in 3 to 8 days, but this can be changed as appropriate depending on other culture conditions.
培養物からの5−ALAの採取は通常の方法で実施でき
る0例えば、培養物をまず遠心分離して菌体を除去し、
上清のp Hを2.5に調節した後、Na+型のイオン
交換樹脂に吸着させ、pl(5,0のクエン酸ナトリウ
ム・クエン酸v11i液で溶出し、5−ALA画分を濃
縮し、゛必要に応じて更に精製工程を加えればよい。5-ALA can be collected from a culture using a conventional method. For example, the culture is first centrifuged to remove bacterial cells,
After adjusting the pH of the supernatant to 2.5, it was adsorbed onto a Na+ type ion exchange resin, eluted with pl (5,0 sodium citrate/citric acid v11i solution, and the 5-ALA fraction was concentrated. ``A further purification step may be added if necessary.
以下、実施例を以て本発明を説明するが、本発明はこれ
に限定されるものではない。The present invention will be explained below with reference to Examples, but the present invention is not limited thereto.
(実施例)
実施例1
メタノサルシナ バーケリ DSM804を、気相を窒
素で置換した表−1に示す基本培地で37℃、60時間
培養した。培養後、遠心分離により除菌し、得られた上
清液について生産された5−ALAを測定した結果、0
.8■/1の5−ALAが得られた。(Example) Example 1 Methanosarcina Berkeli DSM804 was cultured at 37°C for 60 hours in the basal medium shown in Table 1 in which the gas phase was replaced with nitrogen. After culturing, the bacteria were removed by centrifugation, and the amount of 5-ALA produced in the resulting supernatant was measured, and the result was 0.
.. 5-ALA of 8.1/1 was obtained.
実施例2
メタノサルシナ バーケリ DSM804を、実施例1
と同様に培養し、その6mlを表−2に示した各濃度の
4.6−シケトヘブタン酸を含有する基本培地にそれぞ
れ接種し、嫌気条件下で37℃。Example 2 Methanosarcina barkeri DSM804 was added to Example 1
6 ml of the culture was inoculated into a basal medium containing each concentration of 4.6-siketohebutanoic acid shown in Table 2, and the mixture was incubated at 37°C under anaerobic conditions.
80時間培養した。5−ALAの生成量および菌体生宵
量を表−2に示した。Cultured for 80 hours. The production amount of 5-ALA and the bacterial cell yield are shown in Table 2.
実施例3
メタノサルシナ バーケリ DSM804を、実施例1
と同様に培養し、その6mlを表−3に示した各濃度の
レブリン酸を含有する基本培地にそれぞれ接種し、嫌気
条件下で37℃、80時間培養した。5−ALAの生成
量および菌体生冑量を表−3に示した。Example 3 Methanosarcina barkeri DSM804 was added to Example 1
The cells were cultured in the same manner as above, and 6 ml of the culture was inoculated into a basal medium containing each concentration of levulinic acid shown in Table 3, and cultured under anaerobic conditions at 37°C for 80 hours. The amount of 5-ALA produced and the amount of bacterial biomass are shown in Table 3.
実施例4
メタノサルシナ バーケリ DSM804を、実施例1
と同様に培養し、その6 mlをレブリン酸20mH,
L−アラニン15nNおよび表−4に示した各濃度のα
−ケトグルタル酸を含有する基本培地にそれぞれ接種し
、嫌気条件下で37℃、 80時間培養した。5−AL
Aの生成量および菌体生冑量を表−4に示した。Example 4 Methanosarcina barkeri DSM804 was added to Example 1
Culture in the same manner as above, add 6 ml of levulinic acid to 20 mH of levulinic acid,
L-alanine 15 nN and α of each concentration shown in Table 4
- They were each inoculated into a basal medium containing ketoglutaric acid and cultured at 37°C for 80 hours under anaerobic conditions. 5-AL
The production amount of A and the amount of bacterial cell culture are shown in Table 4.
実施例5
メタノサルシナ バーケリ DSM804を、実施例1
と同様に培養し、その8.5mlを、担体として多孔性
シリカ(ナガオポーセル、長尾曹達■製)を充填し基本
培地を満たした基型リアクターに接種し、37℃、48
時間培養した。その後、表−5に示した各濃度のレブリ
ン酸を含有する基本培地をそれぞれ連続的に供給した。Example 5 Methanosarcina barkeri DSM804 was added to Example 1
8.5 ml of the culture was inoculated into a base reactor filled with porous silica (Nagao Porcel, manufactured by Nagao Soda) as a carrier and basic medium, and incubated at 37°C and 48°C.
Cultured for hours. Thereafter, basal medium containing levulinic acid at each concentration shown in Table 5 was continuously supplied.
供給速度は最終的に希釈率13.1/daVに固定した
。定常値における5−ALA生産性を表−5に示した。The feed rate was finally fixed at a dilution rate of 13.1/daV. 5-ALA productivity at steady-state values is shown in Table-5.
表−1基本培地組成
イミダゾール 5.44 gK2)
IPO40,6961r
KM2PO40,454g
NH4C11、OOt
MgS04・7 H201−005r
NaC14,5g
CaC1・2H200,25g
Fe50 ・7H204,0■
Na25ea3 o、04 MMn
Cl ・4 H200,125+wビタミン溶液 1
) 20 mlミネラル溶液 2
)6ml
クエン酸チタニウム 0 、075+eno
lL−システィン・塩酸 0.3 gメタ
ノール 8 gj
pH6,3〜6.8
1) ビタミン溶液
ビオチン 2N
葉酸 2゜
ピリドキシン・塩a 10■チアミン・塩酸
5■
リボフラビン 5■
ニコチン酸 5■
パントテン酸カルシウム 5、
P−アミノ安息香酸 5mgリポ酸
5N 112) ミネラル溶液
Z n 5040 、 1 g
MnCl ・4H200,04g
H3BO40,3g
Coal ・6HO0,2g
Cue 12 ・2H200−01t
NiCl2・6 H2・0 0 、02 、tNi
Cl ・6 H200、02t
NaMoO4−2H200,03g 11表−2
表−3
表−4
表−5
(発明の効果)
本発明により、経済的に有利な方法で5−ALAを製造
することが可能になった。Table-1 Basic medium composition Imidazole 5.44 gK2)
IPO40,6961r KM2PO40,454g NH4C11,OOt MgS04・7 H201-005r NaC14,5g CaC1・2H200,25g Fe50 ・7H204,0■ Na25ea3 o,04 MMn
Cl ・4 H200,125+w vitamin solution 1
) 20ml mineral solution 2
)6ml titanium citrate 0,075+eno
1L-cysteine/hydrochloric acid 0.3 g methanol 8 gj pH6.3-6.8 1) Vitamin solution biotin 2N folic acid 2゜pyridoxine/salt a 10 ■ Thiamine/hydrochloric acid 5 ■ Riboflavin 5 ■ Nicotinic acid 5 ■ Calcium pantothenate 5 , P-aminobenzoic acid 5mg lipoic acid
5N 112) Mineral solution Z n 5040, 1 g MnCl ・4H200,04g H3BO40,3g Coal ・6HO0,2g Cue 12 ・2H200-01t NiCl2・6 H2・0 0 ,02 ,tNi
Cl ・6 H200,02t NaMoO4-2H200,03g 11Table-2 Table-3 Table-4 Table-5 (Effect of the invention) The present invention makes it possible to produce 5-ALA in an economically advantageous method. became.
Claims (1)
属し、5−アミノレブリン酸を生産する能力を有する微
生物を培養し、5−アミノレブリン酸を生成させ、これ
を採取することを特徴とする5−アミノレブリン酸の製
造法A method for producing 5-aminolevulinic acid, which comprises culturing a microorganism belonging to the genus Methanosarcina and having the ability to produce 5-aminolevulinic acid, producing 5-aminolevulinic acid, and collecting the same.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP30694087A JPH01148193A (en) | 1987-12-04 | 1987-12-04 | Production of 5-aminolevulic acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP30694087A JPH01148193A (en) | 1987-12-04 | 1987-12-04 | Production of 5-aminolevulic acid |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH01148193A true JPH01148193A (en) | 1989-06-09 |
Family
ID=17963109
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP30694087A Pending JPH01148193A (en) | 1987-12-04 | 1987-12-04 | Production of 5-aminolevulic acid |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH01148193A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06141875A (en) * | 1992-11-08 | 1994-05-24 | Cosmo Sogo Kenkyusho:Kk | Production of 5-aminolevulinic acid by microorganism |
WO2007034673A1 (en) * | 2005-09-21 | 2007-03-29 | Cosmo Oil Co., Ltd. | Process for producing 5-aminolevulinic acid hydrochloride |
JP2012121918A (en) * | 2012-03-08 | 2012-06-28 | Cosmo Oil Co Ltd | Method for producing 5-aminolevulinic acid hydrochloride |
-
1987
- 1987-12-04 JP JP30694087A patent/JPH01148193A/en active Pending
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06141875A (en) * | 1992-11-08 | 1994-05-24 | Cosmo Sogo Kenkyusho:Kk | Production of 5-aminolevulinic acid by microorganism |
WO2007034673A1 (en) * | 2005-09-21 | 2007-03-29 | Cosmo Oil Co., Ltd. | Process for producing 5-aminolevulinic acid hydrochloride |
JP2007084466A (en) * | 2005-09-21 | 2007-04-05 | Cosmo Oil Co Ltd | Method for producing 5-aminolevulinic acid hydrochloride |
US8148574B2 (en) | 2005-09-21 | 2012-04-03 | Cosmo Oil Co., Ltd. | Method for producing 5-aminolevulinic acid hydrochloride |
JP2012121918A (en) * | 2012-03-08 | 2012-06-28 | Cosmo Oil Co Ltd | Method for producing 5-aminolevulinic acid hydrochloride |
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