JPS644760B2 - - Google Patents
Info
- Publication number
- JPS644760B2 JPS644760B2 JP55186819A JP18681980A JPS644760B2 JP S644760 B2 JPS644760 B2 JP S644760B2 JP 55186819 A JP55186819 A JP 55186819A JP 18681980 A JP18681980 A JP 18681980A JP S644760 B2 JPS644760 B2 JP S644760B2
- Authority
- JP
- Japan
- Prior art keywords
- spp
- group
- formula
- ester
- bacterial cells
- 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.)
- Expired
Links
- 150000002148 esters Chemical class 0.000 claims description 17
- 230000001580 bacterial effect Effects 0.000 claims description 16
- 238000006460 hydrolysis reaction Methods 0.000 claims description 11
- -1 t-butoxycarbonyl group Chemical group 0.000 claims description 10
- 244000005700 microbiome Species 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 241000159512 Geotrichum Species 0.000 claims description 5
- 241000235648 Pichia Species 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 241000235395 Mucor Species 0.000 claims description 3
- 241000228143 Penicillium Species 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims description 2
- 241000235389 Absidia Species 0.000 claims description 2
- 241000228212 Aspergillus Species 0.000 claims description 2
- 241000186146 Brevibacterium Species 0.000 claims description 2
- 241001450911 Circinella Species 0.000 claims description 2
- 241000235555 Cunninghamella Species 0.000 claims description 2
- 241000223218 Fusarium Species 0.000 claims description 2
- 241000588731 Hafnia Species 0.000 claims description 2
- 241000192041 Micrococcus Species 0.000 claims description 2
- 241000588769 Proteus <enterobacteria> Species 0.000 claims description 2
- 241000223230 Trichosporon Species 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- 210000000078 claw Anatomy 0.000 claims description 2
- 238000007796 conventional method Methods 0.000 claims description 2
- CJNBYAVZURUTKZ-UHFFFAOYSA-N hafnium(IV) oxide Inorganic materials O=[Hf]=O CJNBYAVZURUTKZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- CTLHFZBIZFOLIK-BYPYZUCNSA-N (3s)-3-amino-5-methoxy-5-oxopentanoic acid Chemical compound COC(=O)C[C@@H](N)CC(O)=O CTLHFZBIZFOLIK-BYPYZUCNSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000006285 cell suspension Substances 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- RBOKYBCBRQCEHG-NSHDSACASA-N (3s)-5-methoxy-5-oxo-3-(phenylmethoxycarbonylamino)pentanoic acid Chemical compound COC(=O)C[C@H](CC(O)=O)NC(=O)OCC1=CC=CC=C1 RBOKYBCBRQCEHG-NSHDSACASA-N 0.000 description 2
- RBOKYBCBRQCEHG-UHFFFAOYSA-N 5-methoxy-5-oxo-3-(phenylmethoxycarbonylamino)pentanoic acid Chemical compound COC(=O)CC(CC(O)=O)NC(=O)OCC1=CC=CC=C1 RBOKYBCBRQCEHG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241001305961 Lichtheimia hyalospora Species 0.000 description 2
- 241000191938 Micrococcus luteus Species 0.000 description 2
- 241000235042 Millerozyma farinosa Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 241000588770 Proteus mirabilis Species 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DQCHMKBHICLFSB-YFKPBYRVSA-N (3s)-3-amino-5-ethoxy-5-oxopentanoic acid Chemical compound CCOC(=O)C[C@@H](N)CC(O)=O DQCHMKBHICLFSB-YFKPBYRVSA-N 0.000 description 1
- DQCHMKBHICLFSB-UHFFFAOYSA-N 3-amino-5-ethoxy-5-oxopentanoic acid Chemical compound CCOC(=O)CC(N)CC(O)=O DQCHMKBHICLFSB-UHFFFAOYSA-N 0.000 description 1
- 241001019659 Acremonium <Plectosphaerellaceae> Species 0.000 description 1
- 241000908198 Actinomucor Species 0.000 description 1
- 241001634946 Apiotrichum brassicae Species 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 235000012539 Bacterium linens Nutrition 0.000 description 1
- 241000186310 Brevibacterium linens Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000266801 Circinella mucoroides Species 0.000 description 1
- 241000235556 Cunninghamella elegans Species 0.000 description 1
- 241000577840 Fusarium merismoides Species 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
- 241000588729 Hafnia alvei Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000498617 Mucor javanicus Species 0.000 description 1
- 241000638162 Mucor moelleri Species 0.000 description 1
- 241001236817 Paecilomyces <Clavicipitaceae> Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 241000588264 Rhizopus javanicus Species 0.000 description 1
- 241000187693 Rhodococcus rhodochrous Species 0.000 description 1
- 241000698291 Rugosa Species 0.000 description 1
- 241000096008 Thamnostylum nigricans Species 0.000 description 1
- WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 description 1
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 1
- 241000223231 Trichosporon beigelii Species 0.000 description 1
- 241000306282 Umbelopsis isabellina Species 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 229940041011 carbapenems Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012531 culture fluid Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- SBBXWAKYTDAMJX-UHFFFAOYSA-N diethyl 3-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate Chemical compound C(C)(C)(C)OC(=O)NC(CC(=O)OCC)CC(=O)OCC SBBXWAKYTDAMJX-UHFFFAOYSA-N 0.000 description 1
- GDPOAFNYCGJPME-UHFFFAOYSA-N dimethyl 2-(phenylmethoxycarbonylamino)pentanedioate Chemical compound COC(=O)CCC(C(=O)OC)NC(=O)OCC1=CC=CC=C1 GDPOAFNYCGJPME-UHFFFAOYSA-N 0.000 description 1
- GCARTCPMCGRKDU-UHFFFAOYSA-N dimethyl 3-(phenylmethoxycarbonylamino)pentanedioate Chemical compound COC(=O)CC(CC(=O)OC)NC(=O)OCC1=CC=CC=C1 GCARTCPMCGRKDU-UHFFFAOYSA-N 0.000 description 1
- LNVSVQDYUJMTGQ-UHFFFAOYSA-N dimethyl 3-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate Chemical compound COC(=O)CC(CC(=O)OC)NC(=O)OC(C)(C)C LNVSVQDYUJMTGQ-UHFFFAOYSA-N 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000013028 medium composition Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
- SEWIYICDCVPBEW-UHFFFAOYSA-N methyl glutamate Chemical compound COC(=O)C(N)CCC(O)=O SEWIYICDCVPBEW-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000004809 thin layer chromatography 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
- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55186819A JPS57115184A (en) | 1980-12-30 | 1980-12-30 | Preparation of optical active (s)-beta-aminoglutaric acid monoalkyl ester |
| US06/328,696 US4415657A (en) | 1980-12-30 | 1981-12-08 | Process for preparation of an optically active monoalkyl ester of β-(S)-aminoglutaric acid |
| GB8137930A GB2090592B (en) | 1980-12-30 | 1981-12-16 | Process for preparation of an optically active monoalkyl ester of b-(s)-aminoglutaric acid |
| DE19813150810 DE3150810A1 (de) | 1980-12-30 | 1981-12-22 | Verfahren zur herstellung eines optische aktiven monoalkylesters der ss-(s)-aminoglutarsaeure |
| BE0/206941A BE891632A (fr) | 1980-12-30 | 1981-12-28 | Procede de preparation d'esters monoalkyliques optiquement actifs de l'acide ???-(s)-aminoglutarique |
| FR8124534A FR2497230A1 (fr) | 1980-12-30 | 1981-12-30 | Procede de preparation d'esters monoalkyliques optiquement actifs d'acide b-(s)-aminoglutarique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55186819A JPS57115184A (en) | 1980-12-30 | 1980-12-30 | Preparation of optical active (s)-beta-aminoglutaric acid monoalkyl ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57115184A JPS57115184A (en) | 1982-07-17 |
| JPS644760B2 true JPS644760B2 (zh) | 1989-01-26 |
Family
ID=16195147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55186819A Granted JPS57115184A (en) | 1980-12-30 | 1980-12-30 | Preparation of optical active (s)-beta-aminoglutaric acid monoalkyl ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57115184A (zh) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59205989A (ja) * | 1983-05-09 | 1984-11-21 | Sumitomo Chem Co Ltd | 光学活性なアルコ−ル化合物の生化学的製法 |
-
1980
- 1980-12-30 JP JP55186819A patent/JPS57115184A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57115184A (en) | 1982-07-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0197474B1 (en) | Process for preparing optically active indoline-2-carboxylic acid | |
| EP0130752B1 (en) | Process for preparing optically active carboxylic acids and antipode esters thereof | |
| US4415657A (en) | Process for preparation of an optically active monoalkyl ester of β-(S)-aminoglutaric acid | |
| WO1994020635A1 (en) | Enantioselective hydrolysis of ketoprofen esters by beauveria bassiana and enzymes derived therefrom | |
| JPS644760B2 (zh) | ||
| JPS63245694A (ja) | 光学活性含硫カルボン酸およびその対掌体エステルの製法 | |
| EP0289804A2 (en) | Process for preparing optically active mercapto compound | |
| JPH0242477B2 (zh) | ||
| JP2964163B2 (ja) | Ｒ（―）―１，３―ブタンジオールの製造法 | |
| JP2005117905A (ja) | 光学活性１−ベンジル−３−ピロリジノールの製造方法 | |
| JPS6012992A (ja) | 光学活性カルボン酸の製造法 | |
| JP2007117034A (ja) | 光学活性ニペコチン酸化合物の製造方法 | |
| US5861304A (en) | Process for the enzymatic separation of enantiomers of rac-2-oxotricyclo 2.2.1.0 3,5! heptane-7-carboxylic acid and of rac-2-oxotricyclo 2.2.1.0 3,5! heptane-7-carboxylic esters | |
| JP3218772B2 (ja) | アセチレンアルコール類の製造法 | |
| JP2639651B2 (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 | |
| JP3679819B2 (ja) | （ｓ）−３−（２−チエニルチオ）ブタン酸の製造法 | |
| JPS6094091A (ja) | 光学活性カルボン酸エステルの製造法 | |
| JP3217301B2 (ja) | 光学活性グリシド酸エステル及び光学活性グリセリン酸エステルの製造方法 | |
| JP3893721B2 (ja) | 光学活性化合物の製造方法 | |
| JPH0573396B2 (zh) | ||
| JPH04252189A (ja) | ベンゼンジカルボン酸モノエステルまたはその誘導体の製造方法 | |
| EP0783039A1 (en) | Process for producing optically active 2-alkoxycyclohexanol derivatives | |
| JPS5942888A (ja) | 術生物によるエステル結合加水分解酵素の製造法 | |
| JP3126063B2 (ja) | Ｄ−パントラクトンの製造法 | |
| JP3024361B2 (ja) | 光学活性ピロリジン類の製造法 |