CA1069844A - Method for the preparation of d-carbamyl amino-acids and the corresponding d-aminoacids - Google Patents
Method for the preparation of d-carbamyl amino-acids and the corresponding d-aminoacidsInfo
- Publication number
- CA1069844A CA1069844A CA251,975A CA251975A CA1069844A CA 1069844 A CA1069844 A CA 1069844A CA 251975 A CA251975 A CA 251975A CA 1069844 A CA1069844 A CA 1069844A
- Authority
- CA
- Canada
- Prior art keywords
- carbamyl
- aminoacids
- preparation
- aminoacid
- grams
- 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
- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 150000008574 D-amino acids Chemical class 0.000 title claims abstract 4
- 235000001014 amino acid Nutrition 0.000 claims abstract description 12
- 230000007062 hydrolysis Effects 0.000 claims abstract description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 9
- 210000004185 liver Anatomy 0.000 claims abstract description 6
- 244000309466 calf Species 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 102000004190 Enzymes Human genes 0.000 claims description 5
- 108090000790 Enzymes Proteins 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- -1 hydrocarbon radicals Chemical class 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 230000007071 enzymatic hydrolysis Effects 0.000 claims 2
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 150000001469 hydantoins Chemical class 0.000 abstract description 3
- 230000000875 corresponding effect Effects 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000047 product Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000007792 addition Methods 0.000 description 6
- 229940091173 hydantoin Drugs 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 102000004157 Hydrolases Human genes 0.000 description 4
- 108090000604 Hydrolases Proteins 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- KKLMJYDGZSAIQX-UHFFFAOYSA-N 2-(n-hydroxyanilino)acetic acid Chemical compound OC(=O)CN(O)C1=CC=CC=C1 KKLMJYDGZSAIQX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910017974 NH40H Inorganic materials 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 230000006340 racemization Effects 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GIOUOHDKHHZWIQ-UHFFFAOYSA-N 2-(carbamoylamino)-2-phenylacetic acid Chemical compound NC(=O)NC(C(O)=O)C1=CC=CC=C1 GIOUOHDKHHZWIQ-UHFFFAOYSA-N 0.000 description 1
- LJCWONGJFPCTTL-UHFFFAOYSA-N 4-hydroxyphenylglycine Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-UHFFFAOYSA-N 0.000 description 1
- UMTNMIARZPDSDI-UHFFFAOYSA-N 5-(4-hydroxyphenyl)imidazolidine-2,4-dione Chemical compound C1=CC(O)=CC=C1C1C(=O)NC(=O)N1 UMTNMIARZPDSDI-UHFFFAOYSA-N 0.000 description 1
- NXQJDVBMMRCKQG-UHFFFAOYSA-N 5-phenylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)NC1C1=CC=CC=C1 NXQJDVBMMRCKQG-UHFFFAOYSA-N 0.000 description 1
- FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 1
- 108700023418 Amidases Proteins 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 1
- 101100130497 Drosophila melanogaster Mical gene Proteins 0.000 description 1
- 235000014309 Eleocharis tuberosa Nutrition 0.000 description 1
- 244000103152 Eleocharis tuberosa Species 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 1
- 101100345589 Mus musculus Mical1 gene Proteins 0.000 description 1
- 102000003940 Occludin Human genes 0.000 description 1
- 108090000304 Occludin Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000014030 Podocarpus spicatus Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 102000005922 amidase Human genes 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT23202/75A IT1046399B (it) | 1975-05-12 | 1975-05-12 | Procedimento per la preparazione di d carbamil amminoacidi e dei corrispondenti d amminoacidi |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1069844A true CA1069844A (en) | 1980-01-15 |
Family
ID=11204838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA251,975A Expired CA1069844A (en) | 1975-05-12 | 1976-05-06 | Method for the preparation of d-carbamyl amino-acids and the corresponding d-aminoacids |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS51139687A (cs) |
| AU (1) | AU502568B2 (cs) |
| BE (1) | BE841750A (cs) |
| CA (1) | CA1069844A (cs) |
| CS (1) | CS209871B2 (cs) |
| DD (1) | DD125069A6 (cs) |
| DE (1) | DE2621076B2 (cs) |
| DK (1) | DK208776A (cs) |
| FR (1) | FR2310986A2 (cs) |
| GB (1) | GB1506067A (cs) |
| HU (1) | HU178336B (cs) |
| IT (1) | IT1046399B (cs) |
| LU (1) | LU74912A1 (cs) |
| NL (1) | NL7605081A (cs) |
| NO (1) | NO149779C (cs) |
| SE (1) | SE7605429L (cs) |
| SU (1) | SU784761A3 (cs) |
| YU (1) | YU39038B (cs) |
| ZA (1) | ZA762783B (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5344690A (en) * | 1976-02-04 | 1978-04-21 | Kanegafuchi Chem Ind Co Ltd | Preparation of d-n-carbamylphenylglycine and its substituted derivatives |
| EP0001319A1 (en) * | 1977-08-18 | 1979-04-04 | Beecham Group Plc | Process for the preparation of hydroxyphenyl hydantoin and of hydroxyphenyl glycine, and compounds thus obtained |
| JPS6172762A (ja) * | 1984-09-17 | 1986-04-14 | Kanegafuchi Chem Ind Co Ltd | 光学活性ヒダントイン類の製造法 |
| IT1276163B1 (it) | 1995-11-23 | 1997-10-27 | Eniricerche Spa | Procedimento migliorato per la preparazione di d-alfa-amminoacidi |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT987278B (it) * | 1973-05-11 | 1975-02-20 | Snam Progetti | Procedimento per la preparazione di l carbamil ammino acidi e dei corrispondenti l amminoacidi |
-
1975
- 1975-05-12 IT IT23202/75A patent/IT1046399B/it active
-
1976
- 1976-05-06 AU AU13713/76A patent/AU502568B2/en not_active Expired
- 1976-05-06 CA CA251,975A patent/CA1069844A/en not_active Expired
- 1976-05-10 LU LU74912A patent/LU74912A1/xx unknown
- 1976-05-10 ZA ZA762783A patent/ZA762783B/xx unknown
- 1976-05-11 DK DK208776A patent/DK208776A/da not_active Application Discontinuation
- 1976-05-11 YU YU01182/76A patent/YU39038B/xx unknown
- 1976-05-11 NO NO761621A patent/NO149779C/no unknown
- 1976-05-11 JP JP51052890A patent/JPS51139687A/ja active Granted
- 1976-05-11 GB GB19444/76A patent/GB1506067A/en not_active Expired
- 1976-05-11 HU HU76SA2920A patent/HU178336B/hu unknown
- 1976-05-11 FR FR7614135A patent/FR2310986A2/fr active Granted
- 1976-05-11 DD DD192778A patent/DD125069A6/xx unknown
- 1976-05-11 CS CS763165A patent/CS209871B2/cs unknown
- 1976-05-12 DE DE2621076A patent/DE2621076B2/de not_active Withdrawn
- 1976-05-12 SE SE7605429A patent/SE7605429L/ not_active Application Discontinuation
- 1976-05-12 NL NL7605081A patent/NL7605081A/xx not_active Application Discontinuation
- 1976-05-12 SU SU762356810A patent/SU784761A3/ru active
- 1976-05-12 BE BE166964A patent/BE841750A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| YU118276A (en) | 1982-02-28 |
| AU502568B2 (en) | 1979-08-02 |
| NL7605081A (nl) | 1976-11-16 |
| SU784761A3 (ru) | 1980-11-30 |
| NO149779C (no) | 1984-06-20 |
| NO149779B (no) | 1984-03-12 |
| BE841750A (fr) | 1976-11-12 |
| FR2310986A2 (fr) | 1976-12-10 |
| JPS576912B2 (cs) | 1982-02-08 |
| FR2310986B2 (cs) | 1978-09-01 |
| DE2621076B2 (de) | 1980-04-17 |
| LU74912A1 (cs) | 1977-07-11 |
| DK208776A (da) | 1976-11-13 |
| IT1046399B (it) | 1980-06-30 |
| YU39038B (en) | 1984-02-29 |
| NO761621L (cs) | 1976-11-15 |
| SE7605429L (sv) | 1976-11-13 |
| GB1506067A (en) | 1978-04-05 |
| CS209871B2 (en) | 1981-12-31 |
| ZA762783B (en) | 1977-04-27 |
| DD125069A6 (cs) | 1977-03-30 |
| JPS51139687A (en) | 1976-12-02 |
| HU178336B (en) | 1982-04-28 |
| AU1371376A (en) | 1977-11-10 |
| DE2621076A1 (de) | 1976-11-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |