JPS62195290A - γ−ハロ−β−ヒドロキシ酪酸エステルの製造法 - Google Patents
γ−ハロ−β−ヒドロキシ酪酸エステルの製造法Info
- Publication number
- JPS62195290A JPS62195290A JP3393586A JP3393586A JPS62195290A JP S62195290 A JPS62195290 A JP S62195290A JP 3393586 A JP3393586 A JP 3393586A JP 3393586 A JP3393586 A JP 3393586A JP S62195290 A JPS62195290 A JP S62195290A
- Authority
- JP
- Japan
- Prior art keywords
- halo
- gamma
- ester
- haloacetoacetate
- 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 3
- 150000002148 esters Chemical class 0.000 title abstract description 17
- 244000005700 microbiome Species 0.000 claims abstract description 15
- 241000222068 Sporobolomyces <Sporidiobolaceae> Species 0.000 claims abstract description 6
- 230000001580 bacterial effect Effects 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 2
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 abstract 1
- 241000228393 Sporidiobolus salmonicolor Species 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 11
- -1 β-hydroxybutyric acid ester Chemical class 0.000 description 7
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 230000000813 microbial effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000005695 dehalogenation reaction Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 238000011218 seed culture Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 208000035404 Autolysis Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010057248 Cell death Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 230000000869 mutational effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000028043 self proteolysis Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 238000002525 ultrasonication 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
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3393586A JPS62195290A (ja) | 1986-02-20 | 1986-02-20 | γ−ハロ−β−ヒドロキシ酪酸エステルの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3393586A JPS62195290A (ja) | 1986-02-20 | 1986-02-20 | γ−ハロ−β−ヒドロキシ酪酸エステルの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62195290A true JPS62195290A (ja) | 1987-08-28 |
| JPH0585160B2 JPH0585160B2 (enrdf_load_stackoverflow) | 1993-12-06 |
Family
ID=12400366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3393586A Granted JPS62195290A (ja) | 1986-02-20 | 1986-02-20 | γ−ハロ−β−ヒドロキシ酪酸エステルの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62195290A (enrdf_load_stackoverflow) |
-
1986
- 1986-02-20 JP JP3393586A patent/JPS62195290A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0585160B2 (enrdf_load_stackoverflow) | 1993-12-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2681601A1 (fr) | Polysaccharide, ses applications, son obtention par fermentation, souche de pseudomonas le produisant. | |
| JPS62195290A (ja) | γ−ハロ−β−ヒドロキシ酪酸エステルの製造法 | |
| JP2883712B2 (ja) | 光学活性１，３―ブタンジオールの製法 | |
| JPS5923794B2 (ja) | ジヒドロキシアセトンの製造法 | |
| JP2624296B2 (ja) | γ−ハロ−β−ヒドロキシ酪酸エステルの製造法 | |
| JPH05176785A (ja) | アルブチンの製造法 | |
| JP3079183B2 (ja) | 褐藻分解物の製造法 | |
| JPH0634733B2 (ja) | （Ｒ）−γ−アジド−β−ヒドロキシ酪酸エステルの製造法 | |
| JPH06277079A (ja) | パラトルイル酸の製造方法 | |
| JP3030896B2 (ja) | Ｗｂ９６８物質群およびその製造法 | |
| JPH0591895A (ja) | Ｄ−セリンの製造法 | |
| JPH037587A (ja) | Ｌ―リンゴ酸の製造方法 | |
| LU82370A1 (fr) | Nouvelle substance biologiquement active,sa preparation et les medicaments qui la contiennent | |
| JP3088205B2 (ja) | 光学活性１，３−ブタンジオールの製法 | |
| JPH01191696A (ja) | 光学活性カルボン酸及びその対掌体エステルの製造法 | |
| JPS6359678B2 (enrdf_load_stackoverflow) | ||
| JPH0632635B2 (ja) | 光学活性カルボン酸及びその対掌体エステルの製造法 | |
| JPS6012993A (ja) | 光学活性カルボン酸の製造法 | |
| JPH0424992B2 (enrdf_load_stackoverflow) | ||
| JPS5945894A (ja) | 補酵素ｑ↓１↓０の製造法 | |
| JPH06141856A (ja) | 環状イヌロオリゴ糖及び環状イヌロオリゴ糖生成酵素の製造方法 | |
| JPS62134093A (ja) | カルニチンの製造法 | |
| JPS5953839B2 (ja) | （−）−α−ヒドロキシメチル酪酸の製造方法 | |
| JPS6244915B2 (enrdf_load_stackoverflow) | ||
| JPH0380090A (ja) | ２―オキソ―４―フェニル酪酸の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |