JPS6384496A - ４−オキソピメリン酸モノエステルの製造方法 - Google Patents

４−オキソピメリン酸モノエステルの製造方法

Info

Publication number: JPS6384496A
Authority: JP; Japan
Prior art keywords: oxopimelic; genus; oxopimelic acid; acid; pseudomonas
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.): Granted

Application number

JP22926086A

Other languages

English (en)

Japanese (ja)

Other versions

JPH044872B2 (fr

Inventor

Fumio Moriuchi

文夫森内

Hisae Muroi

室井　久恵

Hiroshi Aibe

相部　博史

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.)

Arakawa Chemical Industries Ltd

Original Assignee

Arakawa Chemical Industries 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.)

1986-09-26

Filing date

1986-09-26

Publication date

1988-04-15

1986-09-26 Application filed by Arakawa Chemical Industries Ltd filed Critical Arakawa Chemical Industries Ltd

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

238000004519 manufacturing process Methods 0.000 title claims description 4
UDDSEESQRGPVIL-UHFFFAOYSA-N 4-oxoheptanedioic acid Chemical compound OC(=O)CCC(=O)CCC(O)=O UDDSEESQRGPVIL-UHFFFAOYSA-N 0.000 title abstract description 10
244000005700 microbiome Species 0.000 claims abstract description 11
239000000126 substance Substances 0.000 claims abstract description 11
241000589516 Pseudomonas Species 0.000 claims abstract description 7
241000590020 Achromobacter Species 0.000 claims abstract description 6
241000186216 Corynebacterium Species 0.000 claims abstract description 6
241000589236 Gluconobacter Species 0.000 claims abstract description 6
241000588881 Chromobacterium Species 0.000 claims abstract description 5
241000193830 Bacillus <bacterium> Species 0.000 claims abstract description 4
241000589565 Flavobacterium Species 0.000 claims abstract description 4
239000002253 acid Substances 0.000 claims abstract description 4
241000186063 Arthrobacter Species 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
230000001580 bacterial effect Effects 0.000 claims description 12
-1 4- oxopimelic acid diester Chemical class 0.000 abstract description 9
150000005690 diesters Chemical class 0.000 abstract description 7
239000007864 aqueous solution Substances 0.000 abstract description 4
239000000872 buffer Substances 0.000 abstract description 2
239000003960 organic solvent Substances 0.000 abstract description 2
230000000813 microbial effect Effects 0.000 abstract 2
241000590035 Achromobacter lyticus Species 0.000 abstract 1
241001658024 Microbacterium chocolatum Species 0.000 abstract 1
238000000034 method Methods 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 10
150000001875 compounds Chemical class 0.000 description 10
239000002994 raw material Substances 0.000 description 9
239000000463 material Substances 0.000 description 8
239000000243 solution Substances 0.000 description 7
239000000203 mixture Substances 0.000 description 6
239000008363 phosphate buffer Substances 0.000 description 6
238000005119 centrifugation Methods 0.000 description 5
ZGBUXZJMZBBISR-UHFFFAOYSA-N diethyl 4-oxoheptanedioate Chemical compound CCOC(=O)CCC(=O)CCC(=O)OCC ZGBUXZJMZBBISR-UHFFFAOYSA-N 0.000 description 5
239000002054 inoculum 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
239000013543 active substance Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000002243 precursor Substances 0.000 description 4
241000589539 Brevundimonas diminuta Species 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
239000000284 extract Substances 0.000 description 3
235000013372 meat Nutrition 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 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
108090000371 Esterases Proteins 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
239000001888 Peptone Substances 0.000 description 2
108010080698 Peptones Proteins 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000008272 agar Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000007796 conventional method Methods 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
ADGKRNQPSRFRMX-UHFFFAOYSA-N dipropyl 4-oxoheptanedioate Chemical compound CCCOC(=O)CCC(=O)CCC(=O)OCCC ADGKRNQPSRFRMX-UHFFFAOYSA-N 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
238000010438 heat treatment Methods 0.000 description 2
238000001802 infusion Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019319 peptone Nutrition 0.000 description 2
239000000047 product Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
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
CSFUHKWQBWYEHK-UHFFFAOYSA-N 7-butoxy-4,7-dioxoheptanoic acid Chemical compound CCCCOC(=O)CCC(=O)CCC(O)=O CSFUHKWQBWYEHK-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
241000894006 Bacteria Species 0.000 description 1
101150041968 CDC13 gene Proteins 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
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
241001524188 Glutamicibacter nicotianae Species 0.000 description 1
241000238631 Hexapoda Species 0.000 description 1
229930186686 Jasmolactone Natural products 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 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
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 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
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
235000019219 chocolate Nutrition 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
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
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000008103 glucose Substances 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
239000010656 jasmine oil Substances 0.000 description 1
NBCMACYORPIYNY-UHFFFAOYSA-N jasmolactone Chemical compound CC=CCCC1CCCC(=O)O1 NBCMACYORPIYNY-UHFFFAOYSA-N 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
238000002156 mixing Methods 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
238000012545 processing Methods 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
239000013557 residual solvent Substances 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
230000002194 synthesizing effect Effects 0.000 description 1
229920001059 synthetic polymer Polymers 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 true JPS6384496A (ja)	1988-04-15
JPH044872B2 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
JPH044872B2 (fr)	1992-01-29

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