JPH0558713B2 - - Google Patents

Info

Publication number: JPH0558713B2
Authority: JP; Japan
Prior art keywords: alkylthiophene; acid; reaction; thiopheneacetic acid; thiopheneacetic
Prior art date: 1989-11-08
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

Application number

JP28880889A

Other languages

English (en)

Japanese (ja)

Other versions

JPH03151890A (ja

Inventor

Ikuo Soda

Hajime Satonaka

Seiichi Kaneko

Yoshihiro Sato

Haruo Yugawa

Tetsuya Hiroi

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.)

Kanagawa Prefecture

Original Assignee

Kanagawa Prefecture

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.)

1989-11-08

Filing date

1989-11-08

Publication date

1993-08-27

1989-11-08 Application filed by Kanagawa Prefecture filed Critical Kanagawa Prefecture

1989-11-08 Priority to JP28880889A priority Critical patent/JPH03151890A/ja

1991-06-28 Publication of JPH03151890A publication Critical patent/JPH03151890A/ja

1993-08-27 Publication of JPH0558713B2 publication Critical patent/JPH0558713B2/ja

Status Granted legal-status Critical Current

Links

SMJRBWINMFUUDS-UHFFFAOYSA-N 2-thienylacetic acid Chemical compound OC(=O)CC1=CC=CS1 SMJRBWINMFUUDS-UHFFFAOYSA-N 0.000 claims description 26
238000004519 manufacturing process Methods 0.000 claims description 15
244000005700 microbiome Species 0.000 claims description 11
241000589516 Pseudomonas Species 0.000 claims description 7
241000589774 Pseudomonas sp. Species 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
241000894006 Bacteria Species 0.000 description 10
239000000126 substance Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
238000000034 method Methods 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000002994 raw material Substances 0.000 description 4
229930192474 thiophene Natural products 0.000 description 4
-1 1-methylsulfinyl-1-methylthio-2-thienyl Chemical group 0.000 description 3
OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 3
GOTHKCARNFTUSW-UHFFFAOYSA-N 2-decylthiophene Chemical compound CCCCCCCCCCC1=CC=CS1 GOTHKCARNFTUSW-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 3
239000004202 carbamide Substances 0.000 description 3
CLSHQIDDCJTHAJ-UHFFFAOYSA-N 2-thienylacetonitrile Chemical compound N#CCC1=CC=CS1 CLSHQIDDCJTHAJ-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
229930186147 Cephalosporin Natural products 0.000 description 2
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 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
235000019766 L-Lysine Nutrition 0.000 description 2
239000004472 Lysine Substances 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
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 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
229940124587 cephalosporin Drugs 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
238000012136 culture method Methods 0.000 description 2
238000012258 culturing Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000008103 glucose Substances 0.000 description 2
DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 2
229960000367 inositol Drugs 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000003607 modifier Substances 0.000 description 2
YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 2
229940049954 penicillin Drugs 0.000 description 2
YNCMLFHHXWETLD-UHFFFAOYSA-N pyocyanin Chemical compound CN1C2=CC=CC=C2N=C2C1=CC=CC2=O YNCMLFHHXWETLD-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
YAHHFDSODKFKOV-OTEWLTGOSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;(2r,3r,4s,5s)-2,3,4,5-tetrahydroxyhexanal Chemical compound C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O YAHHFDSODKFKOV-OTEWLTGOSA-N 0.000 description 1
PJVXUVWGSCCGHT-GGJBBHSUSA-N (2r,3s,4s,5r)-2,3,4,5,6-pentahydroxyhexanal;(3s,4r,5r)-1,3,4,5,6-pentahydroxyhexan-2-one Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO PJVXUVWGSCCGHT-GGJBBHSUSA-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
KUWPCJHYPSUOFW-YBXAARCKSA-N 2-nitrophenyl beta-D-galactoside Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1[N+]([O-])=O KUWPCJHYPSUOFW-YBXAARCKSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000004254 Ammonium phosphate Substances 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
KNUPLZAEQXJAQR-UHFFFAOYSA-N C(CC(=O)O)(=O)O.C(C(=O)O)(=O)O.C(=O)O Chemical compound C(CC(=O)O)(=O)O.C(C(=O)O)(=O)O.C(=O)O KNUPLZAEQXJAQR-UHFFFAOYSA-N 0.000 description 1
102000016938 Catalase Human genes 0.000 description 1
108010053835 Catalase Proteins 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
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 1
229920001353 Dextrin Polymers 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
229930091371 Fructose Natural products 0.000 description 1
239000005715 Fructose Substances 0.000 description 1
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 1
108010010803 Gelatin Proteins 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
SRBFZHDQGSBBOR-HWQSCIPKSA-N L-arabinopyranose Chemical compound O[C@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-HWQSCIPKSA-N 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
238000005481 NMR spectroscopy Methods 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
102000015439 Phospholipases Human genes 0.000 description 1
108010064785 Phospholipases Proteins 0.000 description 1
241000589540 Pseudomonas fluorescens Species 0.000 description 1
NGFMICBWJRZIBI-JZRPKSSGSA-N Salicin Natural products O([C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O1)c1c(CO)cccc1 NGFMICBWJRZIBI-JZRPKSSGSA-N 0.000 description 1
241000187747 Streptomyces Species 0.000 description 1
HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
NGFMICBWJRZIBI-UHFFFAOYSA-N alpha-salicin Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=CC=C1CO NGFMICBWJRZIBI-UHFFFAOYSA-N 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 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
239000007864 aqueous solution Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
235000009697 arginine Nutrition 0.000 description 1
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
DLRVVLDZNNYCBX-ZZFZYMBESA-N beta-melibiose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)O1 DLRVVLDZNNYCBX-ZZFZYMBESA-N 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
229940041514 candida albicans extract Drugs 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
235000021466 carotenoid Nutrition 0.000 description 1
150000001747 carotenoids Chemical class 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000007265 chloromethylation reaction Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
235000019425 dextrin Nutrition 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
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
239000012535 impurity Substances 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
238000001802 infusion Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
159000000014 iron salts Chemical class 0.000 description 1
AIHDCSAXVMAMJH-GFBKWZILSA-N levan Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@@H]1[C@@H](O)[C@H](O)[C@](CO)(CO[C@@H]2[C@H]([C@H](O)[C@@](O)(CO)O2)O)O1 AIHDCSAXVMAMJH-GFBKWZILSA-N 0.000 description 1
235000019421 lipase Nutrition 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
229940045184 malt extract Drugs 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000013028 medium composition Substances 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000013379 molasses Nutrition 0.000 description 1
230000004899 motility Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
238000006395 oxidase reaction Methods 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
238000006552 photochemical reaction Methods 0.000 description 1
239000000049 pigment Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
238000000746 purification Methods 0.000 description 1
229940120668 salicin Drugs 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
238000007086 side reaction Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
229910021654 trace metal Chemical class 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1

Landscapes

Micro-Organisms Or Cultivation Processes Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

JP28880889A 1989-11-08 1989-11-08 新規微生物およびそれを用いる２―チオフェン酢酸の製造方法 Granted JPH03151890A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP28880889A JPH03151890A (ja)	1989-11-08	1989-11-08	新規微生物およびそれを用いる２―チオフェン酢酸の製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP28880889A JPH03151890A (ja)	1989-11-08	1989-11-08	新規微生物およびそれを用いる２―チオフェン酢酸の製造方法

Publications (2)

Publication Number	Publication Date
JPH03151890A JPH03151890A (ja)	1991-06-28
JPH0558713B2 true JPH0558713B2 (cs)	1993-08-27

Family

ID=17735000

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP28880889A Granted JPH03151890A (ja)	1989-11-08	1989-11-08	新規微生物およびそれを用いる２―チオフェン酢酸の製造方法

Country Status (1)

Country	Link
JP (1)	JPH03151890A (cs)

1989
- 1989-11-08 JP JP28880889A patent/JPH03151890A/ja active Granted

Also Published As

Publication number	Publication date
JPH03151890A (ja)	1991-06-28

Publication	Publication Date	Title
JPH078235B2 (ja)	1995-02-01	シュードグルコノバクター属酸化菌
JP4394647B2 (ja)	2010-01-06	光学活性テトラヒドロチオフェン誘導体の製造方法、および、光学活性テトラヒドロチオフェン−３−オールの晶析方法
JP3698742B2 (ja)	2005-09-21	光学活性４−ヒドロキシ−２−ケトグルタル酸の製造法
JPS62228287A (ja)	1987-10-07	醗酵法による２−ケト−ｄ−グルカル酸の製造法
JPH0558713B2 (cs)	1993-08-27
JP3944333B2 (ja)	2007-07-11	Ｄ−キロ−イノシトールの新規製造方法
JPH0473998B2 (cs)	1992-11-25
JPH09252765A (ja)	1997-09-30	変異株及び該変異株又は親株を用いるエリスリトールの製造方法
US7579485B2 (en)	2009-08-25	Process for producing lactone
JP4982792B2 (ja)	2012-07-25	光学活性なｄ−ホモセリン及びｄ−ホモセリンラクトンの製造法
JPH0728750B2 (ja)	1995-04-05	微生物によるピラジン酸の水酸化物の製造方法
JP2563074B2 (ja)	1996-12-11	天然型β−フェネチルアルコールの製造法
JPH0379996B2 (cs)	1991-12-20
JPH02207795A (ja)	1990-08-17	新規微生物およびそれを用いる２―チオフェン酢酸の製造方法
JP3020266B2 (ja)	2000-03-15	ホスホマイシンの製造方法
JPS61212587A (ja)	1986-09-20	Ｇ００６９ａ物質
JPH05328978A (ja)	1993-12-14	ゼアキサンチンの製造法及びこれに用いる新規フレキシバクター属微生物
JPS6312598B2 (cs)	1988-03-19
JPH0469999B2 (cs)	1992-11-09
JPH09107983A (ja)	1997-04-28	ヒドロキシメチルナフタレン類の製造法ならびにヒドロキシメチルメチルナフタレン類および／またはジヒドロキシメチルナフタレン類の製造法
JPS6325578B2 (cs)	1988-05-26
JPS6134797B2 (cs)	1986-08-09
JPH0539B2 (cs)	1993-01-05
JPH06165695A (ja)	1994-06-14	光学活性２−ヒドロキシアリール酢酸およびその誘導体の製造方法
JPH053792A (ja)	1993-01-14	３−メチル−ｎ−（２−フエニルエチル）−ブタン酸アミドの製造方法及びそれに用いる微生物