JPS60188085A - Ｌ（＋）−β−ヒドロキシ樹肪酸の製造法 - Google Patents
Ｌ（＋）−β−ヒドロキシ樹肪酸の製造法Info
- Publication number
- JPS60188085A JPS60188085A JP59044753A JP4475384A JPS60188085A JP S60188085 A JPS60188085 A JP S60188085A JP 59044753 A JP59044753 A JP 59044753A JP 4475384 A JP4475384 A JP 4475384A JP S60188085 A JPS60188085 A JP S60188085A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- microorganisms
- substrate
- alcohol
- beta
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 18
- 239000002253 acid Substances 0.000 title abstract description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 34
- 229930195729 fatty acid Natural products 0.000 claims abstract description 34
- 239000000194 fatty acid Substances 0.000 claims abstract description 34
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
- 235000015097 nutrients Nutrition 0.000 claims abstract description 10
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims abstract description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 241000178951 Endomyces Species 0.000 claims abstract description 5
- WHBMMWSBFZVSSR-UHFFFAOYSA-N R3HBA Natural products CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 claims abstract description 5
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims abstract description 4
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000004671 saturated fatty acids Chemical class 0.000 claims abstract description 3
- 241000235648 Pichia Species 0.000 claims abstract 2
- 244000005700 microbiome Species 0.000 claims description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 15
- 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 claims description 12
- 239000008103 glucose Substances 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 12
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 10
- 229960004275 glycolic acid Drugs 0.000 claims description 7
- 241000352744 Magnusiomyces tetrasperma Species 0.000 claims description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 6
- 241001482237 Pica Species 0.000 claims description 6
- 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 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229940005605 valeric acid Drugs 0.000 claims description 5
- YIYBQIKDCADOSF-UHFFFAOYSA-N alpha-Butylen-alpha-carbonsaeure Natural products CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 claims description 3
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 claims description 3
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 abstract description 2
- 230000000813 microbial effect Effects 0.000 abstract 2
- 231100000219 mutagenic Toxicity 0.000 abstract 1
- 230000003505 mutagenic effect Effects 0.000 abstract 1
- 230000035755 proliferation Effects 0.000 abstract 1
- 239000002609 medium Substances 0.000 description 19
- 230000035772 mutation Effects 0.000 description 9
- 230000001580 bacterial effect Effects 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- -1 ethyl β-ketovalerate Chemical compound 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- REKYPYSUBKSCAT-UHFFFAOYSA-N 3-hydroxypentanoic acid Chemical compound CCC(O)CC(O)=O REKYPYSUBKSCAT-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- 241000238366 Cephalopoda Species 0.000 description 1
- 241000235035 Debaryomyces Species 0.000 description 1
- 241000150860 Hyphopichia burtonii Species 0.000 description 1
- VZUNGTLZRAYYDE-UHFFFAOYSA-N N-methyl-N'-nitro-N-nitrosoguanidine Chemical compound O=NN(C)C(=N)N[N+]([O-])=O VZUNGTLZRAYYDE-UHFFFAOYSA-N 0.000 description 1
- 241000589776 Pseudomonas putida Species 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 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
- 229960002685 biotin Drugs 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000005251 gamma ray Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
- 229910000357 manganese(II) sulfate Inorganic materials 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 230000037323 metabolic rate Effects 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920003176 water-insoluble polymer Polymers 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59044753A JPS60188085A (ja) | 1984-03-07 | 1984-03-07 | Ｌ（＋）−β−ヒドロキシ樹肪酸の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59044753A JPS60188085A (ja) | 1984-03-07 | 1984-03-07 | Ｌ（＋）−β−ヒドロキシ樹肪酸の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60188085A true JPS60188085A (ja) | 1985-09-25 |
| JPH048035B2 JPH048035B2 (enrdf_load_stackoverflow) | 1992-02-13 |
Family
ID=12700196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59044753A Granted JPS60188085A (ja) | 1984-03-07 | 1984-03-07 | Ｌ（＋）−β−ヒドロキシ樹肪酸の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60188085A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995012683A1 (en) * | 1993-11-03 | 1995-05-11 | Gist-Brocades N.V. | Microbial strains producing sphingolipid bases |
-
1984
- 1984-03-07 JP JP59044753A patent/JPS60188085A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995012683A1 (en) * | 1993-11-03 | 1995-05-11 | Gist-Brocades N.V. | Microbial strains producing sphingolipid bases |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH048035B2 (enrdf_load_stackoverflow) | 1992-02-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1100896A (en) | Microbiological methods | |
| US5254467A (en) | Fermentive production of 1,3-propanediol | |
| CA2236472A1 (en) | A mutant e. coli strain with increased succinic acid production | |
| JP2009521918A (ja) | 長鎖ジカルボン酸の製造方法 | |
| JPH0365192A (ja) | １，３―プロパンジオールの発酵的製法 | |
| JPS61254193A (ja) | 不飽和ワツクスエステルの製造方法 | |
| JPH0775589A (ja) | プロトカテキュ酸の製造方法 | |
| JPS6257313B2 (enrdf_load_stackoverflow) | ||
| JPS60188085A (ja) | Ｌ（＋）−β−ヒドロキシ樹肪酸の製造法 | |
| JPH03191794A (ja) | 微生物処理によるｒ―（―）―３―ハロゲノ―１，２―プロパンジオールの製法 | |
| US4540665A (en) | Process for producing D-β-hydroxyalkanoic acid | |
| JPS6142560B2 (enrdf_load_stackoverflow) | ||
| JPS58224692A (ja) | Ｄ（−）−β−ヒドロキシ脂肪酸の製造法 | |
| JPH03191795A (ja) | 微生物処理によるｓ―（＋）―３―ハロゲノ―１，２―プロパンジオールの製法 | |
| JPS6142559B2 (enrdf_load_stackoverflow) | ||
| JPS61185193A (ja) | Ｌ（＋）−β−ヒドロキシ脂肪酸の製造法 | |
| JPS63295A (ja) | ニコチンアミドアデニンジヌクレオチドの製造法 | |
| JPS58224693A (ja) | Ｄ（−）−β−ヒドロキシ吉草酸の製造法 | |
| SU553283A1 (ru) | Способ получени алкогольдегидрогеназы | |
| JPS626672A (ja) | バチルス・エスピ−ｔｙ−００７および該微生物を用いるモノカルボン酸の製造法 | |
| JPH02257874A (ja) | ロドコッカス属細菌及びそれを用いる２―ヒドロキシ酪酸の製造法 | |
| JPS6047690A (ja) | 微生物によるジカルボン酸の製造法 | |
| JPS6047677A (ja) | 新規微生物 | |
| JPH04237495A (ja) | ジアルコールの製造方法 | |
| JPS5959197A (ja) | 補酵素ｑ↓１↓０の製造法 |