JPH044872B2 - - Google Patents

Info

Publication number: JPH044872B2
Authority: JP; Japan
Prior art keywords: oxopimelic; oxopimelic acid; acid; ester; nmr
Prior art date: 1986-09-26
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

JP22926086A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6384496A (ja

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.)

1986-09-26

Filing date

1986-09-26

Publication date

1992-01-29

1986-09-26 Application filed filed Critical

1986-09-26 Priority to JP22926086A priority Critical patent/JPS6384496A/ja

1988-04-15 Publication of JPS6384496A publication Critical patent/JPS6384496A/ja

1992-01-29 Publication of JPH044872B2 publication Critical patent/JPH044872B2/ja

Status Granted legal-status Critical Current

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)

JP22926086A 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 Granted JPS6384496A (ja)

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 (fr)	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 (fr)

1986
- 1986-09-26 JP JP22926086A patent/JPS6384496A/ja active Granted

Also Published As

Publication number	Publication date
JPS6384496A (ja)	1988-04-15

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