CS209871B2 - Method of preparation of the d-ureido acids and respective d-amino acids - Google Patents
Method of preparation of the d-ureido acids and respective d-amino acids Download PDFInfo
- Publication number
- CS209871B2 CS209871B2 CS763165A CS316576A CS209871B2 CS 209871 B2 CS209871 B2 CS 209871B2 CS 763165 A CS763165 A CS 763165A CS 316576 A CS316576 A CS 316576A CS 209871 B2 CS209871 B2 CS 209871B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- acids
- ureido
- preparation
- amino acids
- grams
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 11
- 150000008574 D-amino acids Chemical class 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 238000009835 boiling Methods 0.000 claims abstract description 6
- 230000007071 enzymatic hydrolysis Effects 0.000 claims abstract description 6
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 claims abstract description 6
- 244000309466 calf Species 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 10
- 210000004185 liver Anatomy 0.000 abstract description 7
- 229940091173 hydantoin Drugs 0.000 abstract description 5
- 102000004190 Enzymes Human genes 0.000 abstract description 4
- 108090000790 Enzymes Proteins 0.000 abstract description 4
- 150000001413 amino acids Chemical class 0.000 abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 abstract description 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 102000004157 Hydrolases Human genes 0.000 description 6
- 108090000604 Hydrolases Proteins 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000000835 fiber Substances 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- GSHIDXLOTQDUAV-SSDOTTSWSA-N (2r)-2-(carbamoylamino)-2-(4-hydroxyphenyl)acetic acid Chemical compound NC(=O)N[C@@H](C(O)=O)C1=CC=C(O)C=C1 GSHIDXLOTQDUAV-SSDOTTSWSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000008057 potassium phosphate buffer Substances 0.000 description 4
- 239000011541 reaction mixture Substances 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
- 238000000921 elemental analysis Methods 0.000 description 3
- 150000001469 hydantoins Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- BSELETLMMBGICP-MRVPVSSYSA-N (2R)-2-(carbamoylamino)-2-(4-methoxyphenyl)acetic acid Chemical compound COC1=CC=C(C=C1)[C@@H](NC(N)=O)C(O)=O BSELETLMMBGICP-MRVPVSSYSA-N 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 2
- DXCSOTJUBCFLRJ-UHFFFAOYSA-N 5-(4-methoxyphenyl)imidazolidine-2,4-dione Chemical compound C1=CC(OC)=CC=C1C1C(=O)NC(=O)N1 DXCSOTJUBCFLRJ-UHFFFAOYSA-N 0.000 description 2
- GIOUOHDKHHZWIQ-SSDOTTSWSA-N N-carbamoyl-D-phenylglycine Chemical compound NC(=O)N[C@@H](C(O)=O)C1=CC=CC=C1 GIOUOHDKHHZWIQ-SSDOTTSWSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000001311 chemical methods and process Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GXUAKXUIILGDKW-MRVPVSSYSA-N (2r)-2-amino-2-(4-methoxyphenyl)acetic acid Chemical compound COC1=CC=C([C@@H](N)C(O)=O)C=C1 GXUAKXUIILGDKW-MRVPVSSYSA-N 0.000 description 1
- IVWWFWFVSWOTLP-YVZVNANGSA-N (3'as,4r,7'as)-2,2,2',2'-tetramethylspiro[1,3-dioxolane-4,6'-4,7a-dihydro-3ah-[1,3]dioxolo[4,5-c]pyran]-7'-one Chemical compound C([C@@H]1OC(O[C@@H]1C1=O)(C)C)O[C@]21COC(C)(C)O2 IVWWFWFVSWOTLP-YVZVNANGSA-N 0.000 description 1
- BSELETLMMBGICP-UHFFFAOYSA-N 2-(carbamoylamino)-2-(4-methoxyphenyl)acetic acid Chemical compound COC1=CC=C(C(NC(N)=O)C(O)=O)C=C1 BSELETLMMBGICP-UHFFFAOYSA-N 0.000 description 1
- DPZJZJRGYMNBIB-UHFFFAOYSA-N 2-sulfohexanoic acid Chemical compound CCCCC(C(O)=O)S(O)(=O)=O DPZJZJRGYMNBIB-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
- 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
- 108700023418 Amidases Proteins 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- -1 D - (-) - phenylglycine o Chemical class 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 102000005922 amidase Human genes 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000005406 washing Methods 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)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- General Chemical & Material Sciences (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 |
|---|---|
| CS209871B2 true CS209871B2 (en) | 1981-12-31 |
Family
ID=11204838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS763165A CS209871B2 (en) | 1975-05-12 | 1976-05-11 | Method of preparation of the d-ureido acids and respective d-amino acids |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS51139687A (en:Method) |
| AU (1) | AU502568B2 (en:Method) |
| BE (1) | BE841750A (en:Method) |
| CA (1) | CA1069844A (en:Method) |
| CS (1) | CS209871B2 (en:Method) |
| DD (1) | DD125069A6 (en:Method) |
| DE (1) | DE2621076B2 (en:Method) |
| DK (1) | DK208776A (en:Method) |
| FR (1) | FR2310986A2 (en:Method) |
| GB (1) | GB1506067A (en:Method) |
| HU (1) | HU178336B (en:Method) |
| IT (1) | IT1046399B (en:Method) |
| LU (1) | LU74912A1 (en:Method) |
| NL (1) | NL7605081A (en:Method) |
| NO (1) | NO149779C (en:Method) |
| SE (1) | SE7605429L (en:Method) |
| SU (1) | SU784761A3 (en:Method) |
| YU (1) | YU39038B (en:Method) |
| ZA (1) | ZA762783B (en:Method) |
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 ZA ZA762783A patent/ZA762783B/xx unknown
- 1976-05-10 LU LU74912A patent/LU74912A1/xx unknown
- 1976-05-11 GB GB19444/76A patent/GB1506067A/en not_active Expired
- 1976-05-11 JP JP51052890A patent/JPS51139687A/ja active Granted
- 1976-05-11 NO NO761621A patent/NO149779C/no unknown
- 1976-05-11 DD DD192778A patent/DD125069A6/xx unknown
- 1976-05-11 CS CS763165A patent/CS209871B2/cs unknown
- 1976-05-11 DK DK208776A patent/DK208776A/da not_active Application Discontinuation
- 1976-05-11 FR FR7614135A patent/FR2310986A2/fr active Granted
- 1976-05-11 YU YU01182/76A patent/YU39038B/xx unknown
- 1976-05-11 HU HU76SA2920A patent/HU178336B/hu unknown
- 1976-05-12 DE DE2621076A patent/DE2621076B2/de not_active Withdrawn
- 1976-05-12 NL NL7605081A patent/NL7605081A/xx not_active Application Discontinuation
- 1976-05-12 SU SU762356810A patent/SU784761A3/ru active
- 1976-05-12 SE SE7605429A patent/SE7605429L/ not_active Application Discontinuation
- 1976-05-12 BE BE166964A patent/BE841750A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DD125069A6 (en:Method) | 1977-03-30 |
| AU1371376A (en) | 1977-11-10 |
| JPS51139687A (en) | 1976-12-02 |
| SU784761A3 (ru) | 1980-11-30 |
| NO761621L (en:Method) | 1976-11-15 |
| NL7605081A (nl) | 1976-11-16 |
| NO149779C (no) | 1984-06-20 |
| HU178336B (en) | 1982-04-28 |
| NO149779B (no) | 1984-03-12 |
| GB1506067A (en) | 1978-04-05 |
| BE841750A (fr) | 1976-11-12 |
| DK208776A (da) | 1976-11-13 |
| DE2621076B2 (de) | 1980-04-17 |
| SE7605429L (sv) | 1976-11-13 |
| AU502568B2 (en) | 1979-08-02 |
| LU74912A1 (en:Method) | 1977-07-11 |
| FR2310986A2 (fr) | 1976-12-10 |
| YU39038B (en) | 1984-02-29 |
| IT1046399B (it) | 1980-06-30 |
| ZA762783B (en) | 1977-04-27 |
| CA1069844A (en) | 1980-01-15 |
| FR2310986B2 (en:Method) | 1978-09-01 |
| YU118276A (en) | 1982-02-28 |
| DE2621076A1 (de) | 1976-11-25 |
| JPS576912B2 (en:Method) | 1982-02-08 |
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