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 (de) | 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 (de) |
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 |
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