JPS63254988A - ４−オキソピメリン酸モノエステル誘導体の製造方法 - Google Patents
４−オキソピメリン酸モノエステル誘導体の製造方法Info
- Publication number
- JPS63254988A JPS63254988A JP8763287A JP8763287A JPS63254988A JP S63254988 A JPS63254988 A JP S63254988A JP 8763287 A JP8763287 A JP 8763287A JP 8763287 A JP8763287 A JP 8763287A JP S63254988 A JPS63254988 A JP S63254988A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- acid
- group
- oxopimelic
- ethylenedioxypimelic
- 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.)
- Granted
Links
- UDDSEESQRGPVIL-UHFFFAOYSA-N 4-oxoheptanedioic acid Chemical compound OC(=O)CCC(=O)CCC(O)=O UDDSEESQRGPVIL-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- -1 4-oxopimelic acid diester Chemical class 0.000 claims abstract description 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 244000005700 microbiome Species 0.000 claims abstract description 11
- 108090000371 Esterases Proteins 0.000 claims abstract description 6
- 241000589565 Flavobacterium Species 0.000 claims abstract description 6
- 241000589516 Pseudomonas Species 0.000 claims abstract description 6
- 241000589236 Gluconobacter Species 0.000 claims abstract description 5
- 241000193830 Bacillus <bacterium> Species 0.000 claims abstract description 4
- 241000186216 Corynebacterium Species 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 210000004185 liver Anatomy 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 241000186063 Arthrobacter Species 0.000 claims abstract description 3
- 241000588881 Chromobacterium Species 0.000 claims abstract description 3
- 241000590020 Achromobacter Species 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 230000001580 bacterial effect Effects 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 25
- 239000002994 raw material Substances 0.000 abstract description 6
- 239000000284 extract Substances 0.000 abstract description 4
- 235000013372 meat Nutrition 0.000 abstract description 4
- 230000000813 microbial effect Effects 0.000 abstract description 3
- 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 abstract description 2
- 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 abstract description 2
- 239000005018 casein Substances 0.000 abstract description 2
- 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 abstract description 2
- 235000021240 caseins Nutrition 0.000 abstract description 2
- 239000008103 glucose Substances 0.000 abstract description 2
- 239000001963 growth medium Substances 0.000 abstract 1
- 239000002304 perfume Substances 0.000 abstract 1
- 241000894007 species Species 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000002253 acid Substances 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 11
- ONUYCNWYOZCURQ-UHFFFAOYSA-N ethyl 3-[2-(3-ethoxy-3-oxopropyl)-1,3-dioxolan-2-yl]propanoate Chemical compound CCOC(=O)CCC1(CCC(=O)OCC)OCCO1 ONUYCNWYOZCURQ-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000872 buffer Substances 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- 239000003205 fragrance Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 150000005690 diesters Chemical class 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 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 3
- 229920001817 Agar Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002054 inoculum Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000013076 target substance Substances 0.000 description 3
- XTXCCODEPBPXFC-UHFFFAOYSA-N 3-[2-(2-carboxyethyl)-1,3-dioxolan-2-yl]propanoic acid Chemical compound OC(=O)CCC1(CCC(O)=O)OCCO1 XTXCCODEPBPXFC-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 238000006957 Michael reaction Methods 0.000 description 2
- 241001658024 Microbacterium chocolatum Species 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
- 239000000969 carrier Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000000694 effects Effects 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
- 239000003960 organic solvent Substances 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000011218 seed culture Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- 241000590035 Achromobacter lyticus Species 0.000 description 1
- 241000194103 Bacillus pumilus Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000589539 Brevundimonas diminuta Species 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 101000998629 Homo sapiens Importin subunit beta-1 Proteins 0.000 description 1
- 102100033258 Importin subunit beta-1 Human genes 0.000 description 1
- XMLSXPIVAXONDL-PLNGDYQASA-N Jasmone Chemical compound CC\C=C/CC1=C(C)CCC1=O XMLSXPIVAXONDL-PLNGDYQASA-N 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 238000006828 Rosenmund reduction reaction Methods 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 125000004036 acetal group Chemical group 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 238000006359 acetalization reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940023476 agar Drugs 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 238000002306 biochemical method Methods 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 229960005188 collagen Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000012136 culture method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 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
- 239000000725 suspension Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- XMLSXPIVAXONDL-UHFFFAOYSA-N trans-jasmone Natural products CCC=CCC1=C(C)CCC1=O XMLSXPIVAXONDL-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8763287A JPS63254988A (ja) | 1987-04-09 | 1987-04-09 | ４−オキソピメリン酸モノエステル誘導体の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8763287A JPS63254988A (ja) | 1987-04-09 | 1987-04-09 | ４−オキソピメリン酸モノエステル誘導体の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63254988A true JPS63254988A (ja) | 1988-10-21 |
| JPH0369279B2 JPH0369279B2 (enExample) | 1991-10-31 |
Family
ID=13920350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8763287A Granted JPS63254988A (ja) | 1987-04-09 | 1987-04-09 | ４−オキソピメリン酸モノエステル誘導体の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63254988A (enExample) |
-
1987
- 1987-04-09 JP JP8763287A patent/JPS63254988A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0369279B2 (enExample) | 1991-10-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1197484A (en) | Mb-530b derivatives, their preparation and pharmaceutical compositions containing them | |
| Jang et al. | Chemo-enzymatic synthesis of 11-hydroxyundecanoic acid and 1, 11-undecanedioic acid from ricinoleic acid | |
| HU202856B (en) | Process for producing intermediates of 3-dimethyl-mevalonic acid derivatives | |
| UA73774C2 (en) | A method for the preparation of dihydroxy esters and derivatives thereof | |
| US4454330A (en) | Two-functional-group-containing terpenoids, processes for the preparation of the same, and anti-ulcer agents containing the same | |
| CA1173383A (en) | Optically active phenylpropane derivatives, their preparation and their use for the preparation of fungicides | |
| JPS63254988A (ja) | ４−オキソピメリン酸モノエステル誘導体の製造方法 | |
| SU860708A1 (ru) | Способ получени стероидов | |
| JP3149265B2 (ja) | 光学活性な３，５−ジヒドロキシ脂肪酸エステル誘導体の製造法 | |
| US4468458A (en) | Two-functional-group-containing terpenoids, processes for the preparation of the same, and anti-ulcer agents containing the same | |
| 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 | |
| US4456558A (en) | Polyprenyl ketone derivatives | |
| US4592868A (en) | 11-hydroxypregn-4-en-3-one-20-carbaldehyde and a method for its production | |
| US5272069A (en) | Method of producing optically active hydroxyesters | |
| WO1995002061A1 (de) | Verfahren zur biotechnologischen herstellung von alkoholen, aldehyden und carbonsäuren | |
| JP3747640B2 (ja) | 光学活性１，２−ジオール環状炭酸エステルの製造法 | |
| KR910007861A (ko) | 새로운 에스테르 화합물 및 그의 제조방법 | |
| CN109320554B (zh) | 一种实用的乙酰氨基丙烯酸酯类化合物的合成新方法 | |
| JPS6384496A (ja) | ４−オキソピメリン酸モノエステルの製造方法 | |
| JPS60153797A (ja) | メバロン酸の発酵生産法 | |
| JPS6256852B2 (enExample) | ||
| 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 | |
| JPS5953838B2 (ja) | β−ヒドロキシ吉草酸の製造方法 | |
| JPS6363387A (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 | |
| JPH01132393A (ja) | ピメリン酸モノエステル誘導体の製造方法 |