JPH01124398A - 光学活性ヒダントイン類の製造方法 - Google Patents
光学活性ヒダントイン類の製造方法Info
- Publication number
- JPH01124398A JPH01124398A JP23025788A JP23025788A JPH01124398A JP H01124398 A JPH01124398 A JP H01124398A JP 23025788 A JP23025788 A JP 23025788A JP 23025788 A JP23025788 A JP 23025788A JP H01124398 A JPH01124398 A JP H01124398A
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- carbamoyl
- amino acid
- formula
- reaction
- 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
- 150000001469 hydantoins Chemical class 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 244000005700 microbiome Species 0.000 claims abstract description 13
- 102000004190 Enzymes Human genes 0.000 claims abstract description 12
- 108090000790 Enzymes Proteins 0.000 claims abstract description 12
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229940091173 hydantoin Drugs 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000002378 acidificating effect Effects 0.000 claims abstract description 4
- 241000187654 Nocardia Species 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 10
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 5
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 241000186216 Corynebacterium Species 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 241000589158 Agrobacterium Species 0.000 claims description 2
- ZWXPVQSPZVTEJE-UHFFFAOYSA-N 4-(carbamoylamino)-2,3-dihydrochromene-4-carboxylic acid Chemical class C1=CC=C2C(NC(=O)N)(C(O)=O)CCOC2=C1 ZWXPVQSPZVTEJE-UHFFFAOYSA-N 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 150000001923 cyclic compounds Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 abstract description 8
- 150000001413 amino acids Chemical class 0.000 abstract description 7
- 230000003287 optical effect Effects 0.000 abstract description 5
- 230000000707 stereoselective effect Effects 0.000 abstract description 3
- 238000006911 enzymatic reaction Methods 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 53
- 238000000034 method Methods 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000013078 crystal Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- 239000007788 liquid Substances 0.000 description 16
- 230000001580 bacterial effect Effects 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 238000005119 centrifugation Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 235000015097 nutrients Nutrition 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 241000894006 Bacteria Species 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 239000006228 supernatant Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- -1 alkali metal cyanate salt Chemical class 0.000 description 5
- 235000001014 amino acid Nutrition 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 150000001371 alpha-amino acids Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000006285 cell suspension Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 235000013372 meat Nutrition 0.000 description 3
- 239000013028 medium composition Substances 0.000 description 3
- 230000000813 microbial effect Effects 0.000 description 3
- 230000001766 physiological effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 229940035893 uracil Drugs 0.000 description 3
- BTKYMGDWHPJLPY-LBPRGKRZSA-N (2s)-3-(1,3-benzodioxol-5-yl)-2-(carbamoylamino)-2-methylpropanoic acid Chemical compound NC(=O)N[C@@](C(O)=O)(C)CC1=CC=C2OCOC2=C1 BTKYMGDWHPJLPY-LBPRGKRZSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 2
- RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- AQKADTOEOXISQG-JTQLQIEISA-N (2S)-2-(carbamoylamino)-2-phenylpropanoic acid Chemical compound C(N)(=O)N[C@@](C1=CC=CC=C1)(C(=O)O)C AQKADTOEOXISQG-JTQLQIEISA-N 0.000 description 1
- PLFOGGJHQOVQAF-NSHDSACASA-N (4s)-4-(carbamoylamino)-6-fluoro-2,3-dihydrochromene-4-carboxylic acid Chemical compound C1=C(F)C=C2[C@](NC(=O)N)(C(O)=O)CCOC2=C1 PLFOGGJHQOVQAF-NSHDSACASA-N 0.000 description 1
- PGCSVDXEADVLRG-QMMMGPOBSA-N (5s)-5-methyl-5-(2-methylpropyl)imidazolidine-2,4-dione Chemical compound CC(C)C[C@]1(C)NC(=O)NC1=O PGCSVDXEADVLRG-QMMMGPOBSA-N 0.000 description 1
- JNGWGQUYLVSFND-JTQLQIEISA-N (5s)-5-methyl-5-phenylimidazolidine-2,4-dione Chemical compound C=1C=CC=CC=1[C@]1(C)NC(=O)NC1=O JNGWGQUYLVSFND-JTQLQIEISA-N 0.000 description 1
- DBEYNBHRSXVDML-UHFFFAOYSA-N 4-(carbamoylamino)-6-fluoro-2-methyl-2,3-dihydrochromene-4-carboxylic acid Chemical compound FC1=CC=C2OC(C)CC(NC(N)=O)(C(O)=O)C2=C1 DBEYNBHRSXVDML-UHFFFAOYSA-N 0.000 description 1
- SBKRXUMXMKBCLD-UHFFFAOYSA-N 5-(2-methylsulfanylethyl)imidazolidine-2,4-dione Chemical compound CSCCC1NC(=O)NC1=O SBKRXUMXMKBCLD-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 241000186361 Actinobacteria <class> Species 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- 241001430228 Clavibacter sepedonicus Species 0.000 description 1
- 229940127463 Enzyme Inducers Drugs 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
- 241001509401 Gordonia rubripertincta Species 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000002306 biochemical method Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002461 imidazolidines Chemical class 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- CNFDGXZLMLFIJV-UHFFFAOYSA-L manganese(II) chloride tetrahydrate Chemical compound O.O.O.O.[Cl-].[Cl-].[Mn+2] CNFDGXZLMLFIJV-UHFFFAOYSA-L 0.000 description 1
- BHFLUDRTVIDDOR-UHFFFAOYSA-N methyl 2-amino-2-phenylacetate Chemical compound COC(=O)C(N)C1=CC=CC=C1 BHFLUDRTVIDDOR-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23025788A JPH01124398A (ja) | 1988-09-14 | 1988-09-14 | 光学活性ヒダントイン類の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23025788A JPH01124398A (ja) | 1988-09-14 | 1988-09-14 | 光学活性ヒダントイン類の製造方法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59195392A Division JPS6172762A (ja) | 1984-09-17 | 1984-09-17 | 光学活性ヒダントイン類の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01124398A true JPH01124398A (ja) | 1989-05-17 |
| JPH0555117B2 JPH0555117B2 (enrdf_load_stackoverflow) | 1993-08-16 |
Family
ID=16904969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23025788A Granted JPH01124398A (ja) | 1988-09-14 | 1988-09-14 | 光学活性ヒダントイン類の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01124398A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2287152A2 (en) | 2002-06-05 | 2011-02-23 | Kaneka Corporation | Process for producing optically active alpha-methylcysteine derivative |
-
1988
- 1988-09-14 JP JP23025788A patent/JPH01124398A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2287152A2 (en) | 2002-06-05 | 2011-02-23 | Kaneka Corporation | Process for producing optically active alpha-methylcysteine derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0555117B2 (enrdf_load_stackoverflow) | 1993-08-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |