JPH044872B2 - - Google Patents
Info
- Publication number
- JPH044872B2 JPH044872B2 JP22926086A JP22926086A JPH044872B2 JP H044872 B2 JPH044872 B2 JP H044872B2 JP 22926086 A JP22926086 A JP 22926086A JP 22926086 A JP22926086 A JP 22926086A JP H044872 B2 JPH044872 B2 JP H044872B2
- Authority
- JP
- Japan
- Prior art keywords
- oxopimelic
- oxopimelic acid
- acid
- ester
- nmr
- 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
Links
- UDDSEESQRGPVIL-UHFFFAOYSA-N 4-oxoheptanedioic acid Chemical compound OC(=O)CCC(=O)CCC(O)=O UDDSEESQRGPVIL-UHFFFAOYSA-N 0.000 claims description 10
- 244000005700 microbiome Species 0.000 claims description 9
- 108090000371 Esterases Proteins 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 241000589516 Pseudomonas Species 0.000 claims description 4
- 241000589565 Flavobacterium Species 0.000 claims description 3
- 241000589236 Gluconobacter Species 0.000 claims description 3
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- -1 aliphatic dicarboxylic acid diesters Chemical class 0.000 description 11
- 230000001580 bacterial effect Effects 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- ZGBUXZJMZBBISR-UHFFFAOYSA-N diethyl 4-oxoheptanedioate Chemical compound CCOC(=O)CCC(=O)CCC(=O)OCC ZGBUXZJMZBBISR-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 239000008363 phosphate buffer Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000013543 active substance Substances 0.000 description 6
- 241000589539 Brevundimonas diminuta Species 0.000 description 5
- 238000005119 centrifugation Methods 0.000 description 5
- 239000002054 inoculum Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- JYEYJELELKLPLO-UHFFFAOYSA-N 7-ethoxy-4,7-dioxoheptanoic acid Chemical compound CCOC(=O)CCC(=O)CCC(O)=O JYEYJELELKLPLO-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 235000013372 meat Nutrition 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000194103 Bacillus pumilus Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- IUDRJCMDRZEFGO-UHFFFAOYSA-N dimethyl 4-oxoheptanedioate Chemical compound COC(=O)CCC(=O)CCC(=O)OC IUDRJCMDRZEFGO-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- YZBOVSFWWNVKRJ-UHFFFAOYSA-M 2-butoxycarbonylbenzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1C([O-])=O YZBOVSFWWNVKRJ-UHFFFAOYSA-M 0.000 description 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
- BGMLABWFIHLMPM-UHFFFAOYSA-N 4,7-dioxo-7-propoxyheptanoic acid Chemical compound CCCOC(=O)CCC(=O)CCC(O)=O BGMLABWFIHLMPM-UHFFFAOYSA-N 0.000 description 1
- NJWVCUDEAMWIFS-UHFFFAOYSA-N 7-methoxy-4,7-dioxoheptanoic acid Chemical compound COC(=O)CCC(=O)CCC(O)=O NJWVCUDEAMWIFS-UHFFFAOYSA-N 0.000 description 1
- 241000590035 Achromobacter lyticus Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000588881 Chromobacterium Species 0.000 description 1
- NKRWXGPLRNMXKX-UHFFFAOYSA-N Coriolin Natural products CC1(C)CC2C(O)C3(CO3)C45OC4C(=O)C5(C)C2C1O NKRWXGPLRNMXKX-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- ARNPQYFYGKMXGD-UHFFFAOYSA-N Eldanolide Natural products CC1CC(=O)OC1CC=C(C)C ARNPQYFYGKMXGD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241000238631 Hexapoda Species 0.000 description 1
- 238000006898 Intramolecular Friedel-Crafts reaction Methods 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241001658024 Microbacterium chocolatum Species 0.000 description 1
- 241000589587 [Flavobacterium] lutescens Species 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000012062 aqueous buffer Substances 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
- 238000002306 biochemical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- OMAFWWAJLVYWPU-ZOEJUPFXSA-N coriolin Chemical compound O=C([C@H]1O[C@]11[C@@H](O)[C@H]2CC([C@@H]([C@H]2[C@@]11C)O)(C)C)[C@]21CO2 OMAFWWAJLVYWPU-ZOEJUPFXSA-N 0.000 description 1
- 238000012136 culture method Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- MBWFSTYYVKKLMK-UHFFFAOYSA-N dibutyl 4-oxoheptanedioate Chemical compound CCCCOC(=O)CCC(=O)CCC(=O)OCCCC MBWFSTYYVKKLMK-UHFFFAOYSA-N 0.000 description 1
- ADGKRNQPSRFRMX-UHFFFAOYSA-N dipropyl 4-oxoheptanedioate Chemical compound CCCOC(=O)CCC(=O)CCC(=O)OCCC ADGKRNQPSRFRMX-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000011218 seed culture Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22926086A JPS6384496A (ja) | 1986-09-26 | 1986-09-26 | ４−オキソピメリン酸モノエステルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22926086A JPS6384496A (ja) | 1986-09-26 | 1986-09-26 | ４−オキソピメリン酸モノエステルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6384496A JPS6384496A (ja) | 1988-04-15 |
| JPH044872B2 true JPH044872B2 (enExample) | 1992-01-29 |
Family
ID=16889325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22926086A Granted JPS6384496A (ja) | 1986-09-26 | 1986-09-26 | ４−オキソピメリン酸モノエステルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6384496A (enExample) |
-
1986
- 1986-09-26 JP JP22926086A patent/JPS6384496A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6384496A (ja) | 1988-04-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0044158B1 (en) | Novel optically active imidazolidin-2-one derivatives and their production | |
| FR2473519A1 (fr) | Terpenoides contenant deux groupes fonctionnels, leur preparation et leur application therapeutique | |
| EP0501310A1 (en) | Method for optical resolution of corey lactone diols | |
| CA2161849A1 (en) | Production of optically active compounds | |
| SU860708A1 (ru) | Способ получени стероидов | |
| US5773240A (en) | Optically active α-substituted carboxylic acid derivatives and method for producing the same | |
| JPH044872B2 (enExample) | ||
| US4584270A (en) | Process for preparing optically-active 4-amino-3-hydroxybutyric acid | |
| JPH0153039B2 (enExample) | ||
| US4865771A (en) | Process for preparing L(-)-carnitine chloride from 3,4-epoxybutyric esters and novel intermediate compounds | |
| JPH06256278A (ja) | 光学活性α−カルバモイルアルカン酸誘導体およびその製法 | |
| US4613571A (en) | Polyprenyl sulfone derivatives and process for producing the same | |
| US4456558A (en) | Polyprenyl ketone derivatives | |
| JP3452378B2 (ja) | ハロゲン化化合物の製法 | |
| JPS61289899A (ja) | 光学活性２−ハロ−１−フエニルエタノ−ルおよびそのエステルの製造法 | |
| JPH0369279B2 (enExample) | ||
| JPH01132393A (ja) | ピメリン酸モノエステル誘導体の製造方法 | |
| JPH04126089A (ja) | ４―オキソピメリン酸モノエステルの製造法 | |
| JPH0630597B2 (ja) | （Ｒ）―γ―ブチロラクトン―γ―プロピオン酸エステルの製造方法 | |
| WO1999060151A1 (en) | New biotechnological process for preparing hydroxylated ml-236b derivatives, known as m-4 and m-4', and analogues thereof | |
| JPS5945360B2 (ja) | 生理活性物質ｍｌ−２３６ｂの製造法 | |
| EP0431970A2 (en) | Process for producing optically active R-(+)-2, 3,-dichloro-1-propanol using microorganism | |
| JP4042557B2 (ja) | 光学活性テトラヒドロフラン−２−カルボン酸及びそのエステルの製法 | |
| JPH1087613A (ja) | 光学活性アジリン類およびその製造法 | |
| JPS63202398A (ja) | 光学活性シアノヒドリン誘導体の製造方法 |