DE2621076B2 - Verfahren zur Herstellung von D-Aminosäuren - Google Patents
Verfahren zur Herstellung von D-AminosäurenInfo
- Publication number
- DE2621076B2 DE2621076B2 DE2621076A DE2621076A DE2621076B2 DE 2621076 B2 DE2621076 B2 DE 2621076B2 DE 2621076 A DE2621076 A DE 2621076A DE 2621076 A DE2621076 A DE 2621076A DE 2621076 B2 DE2621076 B2 DE 2621076B2
- Authority
- DE
- Germany
- Prior art keywords
- amino acids
- hydrolysis
- reaction
- carbamoyl
- yield
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 11
- 150000008574 D-amino acids Chemical class 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 230000007062 hydrolysis Effects 0.000 claims description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- 229940091173 hydantoin Drugs 0.000 claims description 7
- 210000004185 liver Anatomy 0.000 claims description 6
- 244000309466 calf Species 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000002255 enzymatic effect Effects 0.000 claims description 3
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- 102000004169 proteins and genes Human genes 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 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 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 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 2
- NXQJDVBMMRCKQG-UHFFFAOYSA-N 5-phenylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)NC1C1=CC=CC=C1 NXQJDVBMMRCKQG-UHFFFAOYSA-N 0.000 description 2
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-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
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007071 enzymatic hydrolysis Effects 0.000 description 2
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 2
- 150000001469 hydantoins Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000006340 racemization Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 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
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 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
- 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 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
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- LJCWONGJFPCTTL-SSDOTTSWSA-N D-4-hydroxyphenylglycine Chemical compound [O-]C(=O)[C@H]([NH3+])C1=CC=C(O)C=C1 LJCWONGJFPCTTL-SSDOTTSWSA-N 0.000 description 1
- 101100130497 Drosophila melanogaster Mical gene Proteins 0.000 description 1
- 101100289061 Drosophila melanogaster lili gene Proteins 0.000 description 1
- 235000014309 Eleocharis tuberosa Nutrition 0.000 description 1
- 244000103152 Eleocharis tuberosa 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
- GSHIDXLOTQDUAV-UHFFFAOYSA-N N-Carbamoyl-2-amino-2-(4-hydroxyphenyl)acetic acid Chemical compound NC(=O)NC(C(O)=O)C1=CC=C(O)C=C1 GSHIDXLOTQDUAV-UHFFFAOYSA-N 0.000 description 1
- 235000014030 Podocarpus spicatus Nutrition 0.000 description 1
- 241000220317 Rosa Species 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
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000002699 waste material 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 (2)
| Publication Number | Publication Date |
|---|---|
| DE2621076A1 DE2621076A1 (de) | 1976-11-25 |
| DE2621076B2 true DE2621076B2 (de) | 1980-04-17 |
Family
ID=11204838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2621076A Withdrawn DE2621076B2 (de) | 1975-05-12 | 1976-05-12 | Verfahren zur Herstellung von D-Aminosäuren |
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 ZA ZA762783A patent/ZA762783B/xx unknown
- 1976-05-10 LU LU74912A patent/LU74912A1/xx unknown
- 1976-05-11 FR FR7614135A patent/FR2310986A2/fr active Granted
- 1976-05-11 JP JP51052890A patent/JPS51139687A/ja active Granted
- 1976-05-11 CS CS763165A patent/CS209871B2/cs unknown
- 1976-05-11 YU YU01182/76A patent/YU39038B/xx unknown
- 1976-05-11 DK DK208776A patent/DK208776A/da not_active Application Discontinuation
- 1976-05-11 NO NO761621A patent/NO149779C/no unknown
- 1976-05-11 GB GB19444/76A patent/GB1506067A/en not_active Expired
- 1976-05-11 HU HU76SA2920A patent/HU178336B/hu unknown
- 1976-05-11 DD DD192778A patent/DD125069A6/xx unknown
- 1976-05-12 SU SU762356810A patent/SU784761A3/ru active
- 1976-05-12 DE DE2621076A patent/DE2621076B2/de not_active Withdrawn
- 1976-05-12 BE BE166964A patent/BE841750A/xx not_active IP Right Cessation
- 1976-05-12 SE SE7605429A patent/SE7605429L/ not_active Application Discontinuation
- 1976-05-12 NL NL7605081A patent/NL7605081A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| SU784761A3 (ru) | 1980-11-30 |
| CA1069844A (en) | 1980-01-15 |
| AU502568B2 (en) | 1979-08-02 |
| BE841750A (fr) | 1976-11-12 |
| CS209871B2 (en) | 1981-12-31 |
| IT1046399B (it) | 1980-06-30 |
| DD125069A6 (cs) | 1977-03-30 |
| DK208776A (da) | 1976-11-13 |
| FR2310986A2 (fr) | 1976-12-10 |
| FR2310986B2 (cs) | 1978-09-01 |
| NO149779B (no) | 1984-03-12 |
| AU1371376A (en) | 1977-11-10 |
| YU118276A (en) | 1982-02-28 |
| DE2621076A1 (de) | 1976-11-25 |
| NO761621L (cs) | 1976-11-15 |
| LU74912A1 (cs) | 1977-07-11 |
| JPS576912B2 (cs) | 1982-02-08 |
| NO149779C (no) | 1984-06-20 |
| ZA762783B (en) | 1977-04-27 |
| GB1506067A (en) | 1978-04-05 |
| HU178336B (en) | 1982-04-28 |
| JPS51139687A (en) | 1976-12-02 |
| NL7605081A (nl) | 1976-11-16 |
| SE7605429L (sv) | 1976-11-13 |
| YU39038B (en) | 1984-02-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8228 | New agent |
Free format text: ZUMSTEIN SEN., F., DR. ASSMANN, E., DIPL.-CHEM. DR.RER.NAT. KLINGSEISEN, F., DIPL.-ING. ZUMSTEIN JUN., F., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 8000 MUENCHEN |
|
| 8239 | Disposal/non-payment of the annual fee |