JPS61146191A - （Ｓ）−γ−ハロ−β−ヒドロキシ酪酸エステルの製造法 - Google Patents
（Ｓ）−γ−ハロ−β−ヒドロキシ酪酸エステルの製造法Info
- Publication number
- JPS61146191A JPS61146191A JP27027284A JP27027284A JPS61146191A JP S61146191 A JPS61146191 A JP S61146191A JP 27027284 A JP27027284 A JP 27027284A JP 27027284 A JP27027284 A JP 27027284A JP S61146191 A JPS61146191 A JP S61146191A
- Authority
- JP
- Japan
- Prior art keywords
- halo
- genus
- acid ester
- group
- asymmetric reduction
- 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 17
- 230000000813 microbial effect Effects 0.000 claims abstract description 9
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 241000178951 Endomyces Species 0.000 claims abstract description 3
- 241000223230 Trichosporon Species 0.000 claims abstract description 3
- 241000235648 Pichia Species 0.000 claims abstract 4
- 241000235070 Saccharomyces Species 0.000 claims abstract 2
- 244000005700 microbiome Species 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 230000001580 bacterial effect Effects 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 238000012258 culturing Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 241001030162 Debaryomyces sp. Species 0.000 claims description 2
- 241000159512 Geotrichum Species 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 125000005843 halogen group Chemical group 0.000 abstract description 5
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 230000001766 physiological effect Effects 0.000 abstract description 2
- 241000235035 Debaryomyces Species 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- 230000003287 optical effect Effects 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000758 substrate Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- -1 β-hydroxybutyric acid ester Chemical class 0.000 description 11
- 238000006722 reduction reaction Methods 0.000 description 10
- 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 9
- 239000008103 glucose Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 235000015097 nutrients Nutrition 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 125000001475 halogen functional group Chemical group 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- JJYKJUXBWFATTE-UHFFFAOYSA-N mosher's acid Chemical compound COC(C(O)=O)(C(F)(F)F)C1=CC=CC=C1 JJYKJUXBWFATTE-UHFFFAOYSA-N 0.000 description 4
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000352744 Magnusiomyces tetrasperma Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229940041514 candida albicans extract Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000013028 medium composition Substances 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000012138 yeast extract Substances 0.000 description 3
- ZATUCIUGQZRHSV-UHFFFAOYSA-N 3-oxobutanoic acid;hydrochloride Chemical compound Cl.CC(=O)CC(O)=O ZATUCIUGQZRHSV-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241000222173 Candida parapsilosis Species 0.000 description 2
- 101000841267 Homo sapiens Long chain 3-hydroxyacyl-CoA dehydrogenase Proteins 0.000 description 2
- 102100029107 Long chain 3-hydroxyacyl-CoA dehydrogenase Human genes 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 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 description 2
- 229940055022 candida parapsilosis Drugs 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- ASNHGEVAWNWCRQ-UHFFFAOYSA-N 4-(hydroxymethyl)oxolane-2,3,4-triol Chemical compound OCC1(O)COC(O)C1O ASNHGEVAWNWCRQ-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
- 241000272517 Anseriformes Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 150000004729 acetoacetic acid derivatives Chemical class 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 229940127226 anticholesterol agent Drugs 0.000 description 1
- 150000001277 beta hydroxy acids Chemical class 0.000 description 1
- 150000004718 beta keto acids Chemical class 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27027284A JPS61146191A (ja) | 1984-12-20 | 1984-12-20 | （Ｓ）−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 |
|---|---|---|---|
| JP27027284A JPS61146191A (ja) | 1984-12-20 | 1984-12-20 | （Ｓ）−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 |
|---|---|
| JPS61146191A true JPS61146191A (ja) | 1986-07-03 |
| JPH047195B2 JPH047195B2 (enrdf_load_stackoverflow) | 1992-02-10 |
Family
ID=17483936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27027284A Granted JPS61146191A (ja) | 1984-12-20 | 1984-12-20 | （Ｓ）−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) | JPS61146191A (enrdf_load_stackoverflow) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06153969A (ja) * | 1991-11-07 | 1994-06-03 | Asahi Breweries Ltd | ω−ケト脂肪酸エステル還元法 |
| US5413921A (en) * | 1992-05-28 | 1995-05-09 | Ajinomoto Co., Ltd. | Method of the production of (s)-gamma-halogenated-γ-hydroxybutyric acid esters |
| US5430171A (en) * | 1992-06-02 | 1995-07-04 | Takasago International Corporation | T-butyl (R)-(-)-4-cyano-3-hydroxybutyrate and process for preparing the same |
| EP0606899A3 (en) * | 1993-01-12 | 1995-07-05 | Daicel Chem | Processes for the preparation of optically active 4-halo-3-hydroxy butyric acid esters. |
| WO1998035025A1 (fr) * | 1997-02-07 | 1998-08-13 | Kaneka Corporation | Nouvelle carbonyle reductase, gene codant celle-ci et procede d'utilisation |
| US6001618A (en) * | 1997-12-25 | 1999-12-14 | Daicel Chemical Industries, Ltd. | Haloacetoacetate reductase, method for producing said enzyme, and method for producing alcohols using said enzyme |
| US6168935B1 (en) | 1998-02-25 | 2001-01-02 | Daicel Chemical Industries, Ltd. | Preparation of optically active alcohol substituted with one or more halogen atoms |
| EP1408107A2 (en) | 2002-10-07 | 2004-04-14 | Daiso Co., Ltd. | Chlorohydrin and hydroxycarboxylic ester asymmetric hydrolase gene |
| KR100461561B1 (ko) * | 1998-07-24 | 2005-04-06 | 삼성정밀화학 주식회사 | (s)-3-카르복시-4-브로모부티르산의 제조방법 |
| US7879585B2 (en) | 2006-10-02 | 2011-02-01 | Codexis, Inc. | Ketoreductase enzymes and uses thereof |
-
1984
- 1984-12-20 JP JP27027284A patent/JPS61146191A/ja active Granted
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06153969A (ja) * | 1991-11-07 | 1994-06-03 | Asahi Breweries Ltd | ω−ケト脂肪酸エステル還元法 |
| US5413921A (en) * | 1992-05-28 | 1995-05-09 | Ajinomoto Co., Ltd. | Method of the production of (s)-gamma-halogenated-γ-hydroxybutyric acid esters |
| US5430171A (en) * | 1992-06-02 | 1995-07-04 | Takasago International Corporation | T-butyl (R)-(-)-4-cyano-3-hydroxybutyrate and process for preparing the same |
| EP0606899A3 (en) * | 1993-01-12 | 1995-07-05 | Daicel Chem | Processes for the preparation of optically active 4-halo-3-hydroxy butyric acid esters. |
| US5559030A (en) * | 1993-01-12 | 1996-09-24 | Daicel Chemical Industries, Ltd. | Processes for production of optically active 4-halo-3-hydroxybutyric acid esters |
| US6218156B1 (en) | 1997-02-07 | 2001-04-17 | Kaneka Corporation | Gene encoding carbonyl reductase, and methods for its use |
| WO1998035025A1 (fr) * | 1997-02-07 | 1998-08-13 | Kaneka Corporation | Nouvelle carbonyle reductase, gene codant celle-ci et procede d'utilisation |
| US6448052B2 (en) | 1997-02-07 | 2002-09-10 | Kaneka Corporation | Carbonyl reductase enzyme and methods for its use |
| US6001618A (en) * | 1997-12-25 | 1999-12-14 | Daicel Chemical Industries, Ltd. | Haloacetoacetate reductase, method for producing said enzyme, and method for producing alcohols using said enzyme |
| US6218157B1 (en) | 1997-12-25 | 2001-04-17 | Daicel Chemical Industries, Ltd. | Haloacetoacetate reductase, method for producing said enzyme, and method for producing alcohols using said enzyme |
| US6168935B1 (en) | 1998-02-25 | 2001-01-02 | Daicel Chemical Industries, Ltd. | Preparation of optically active alcohol substituted with one or more halogen atoms |
| KR100461561B1 (ko) * | 1998-07-24 | 2005-04-06 | 삼성정밀화학 주식회사 | (s)-3-카르복시-4-브로모부티르산의 제조방법 |
| EP1408107A2 (en) | 2002-10-07 | 2004-04-14 | Daiso Co., Ltd. | Chlorohydrin and hydroxycarboxylic ester asymmetric hydrolase gene |
| US7879585B2 (en) | 2006-10-02 | 2011-02-01 | Codexis, Inc. | Ketoreductase enzymes and uses thereof |
| US8273547B2 (en) | 2006-10-02 | 2012-09-25 | Codexis, Inc. | Engineered ketoreductases and methods for producing stereoisomerically pure statins |
| US8617864B2 (en) | 2006-10-02 | 2013-12-31 | Codexis, Inc. | Polynucleotides encoding ketoreductases for producing stereoisomerically pure statins and synthetic intermediates therefor |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH047195B2 (enrdf_load_stackoverflow) | 1992-02-10 |
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