DE2460607A1 - Enzymatische hydrolyse von cephalosporinen und enzymatische synthese von halbsynthetischen cephalosporinen - Google Patents
Enzymatische hydrolyse von cephalosporinen und enzymatische synthese von halbsynthetischen cephalosporinenInfo
- Publication number
- DE2460607A1 DE2460607A1 DE19742460607 DE2460607A DE2460607A1 DE 2460607 A1 DE2460607 A1 DE 2460607A1 DE 19742460607 DE19742460607 DE 19742460607 DE 2460607 A DE2460607 A DE 2460607A DE 2460607 A1 DE2460607 A1 DE 2460607A1
- Authority
- DE
- Germany
- Prior art keywords
- enzymatic
- cephalosporins
- reaction
- cephalosporines
- carried out
- 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.)
- Pending
Links
- 230000002255 enzymatic effect Effects 0.000 title claims description 10
- 238000003786 synthesis reaction Methods 0.000 title claims description 10
- 230000015572 biosynthetic process Effects 0.000 title claims description 9
- 230000007071 enzymatic hydrolysis Effects 0.000 title claims description 7
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 title claims description 7
- 150000001780 cephalosporins Chemical class 0.000 claims description 19
- 229930186147 Cephalosporin Natural products 0.000 claims description 18
- 229940124587 cephalosporin Drugs 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 7
- 241000588724 Escherichia coli Species 0.000 claims description 6
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229930182555 Penicillin Natural products 0.000 claims description 3
- 108010073038 Penicillin Amidase Proteins 0.000 claims description 3
- 229940049954 penicillin Drugs 0.000 claims description 3
- 230000001580 bacterial effect Effects 0.000 claims description 2
- 239000008363 phosphate buffer Substances 0.000 claims description 2
- 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
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- NVIAYEIXYQCDAN-UHFFFAOYSA-N 7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)C(N)C12 NVIAYEIXYQCDAN-UHFFFAOYSA-N 0.000 description 10
- 239000008057 potassium phosphate buffer Substances 0.000 description 9
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 8
- 239000002028 Biomass Substances 0.000 description 8
- 239000000284 extract Substances 0.000 description 7
- 238000005119 centrifugation Methods 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 239000001963 growth medium Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- NVIAYEIXYQCDAN-CLZZGJSISA-N 7beta-aminodeacetoxycephalosporanic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](N)[C@@H]12 NVIAYEIXYQCDAN-CLZZGJSISA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 3
- 229940106164 cephalexin Drugs 0.000 description 3
- 108020004256 Beta-lactamase Proteins 0.000 description 2
- 241000588722 Escherichia Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- FUBBGQLTSCSAON-PBFPGSCMSA-N cefaloglycin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)C)C(O)=O)=CC=CC=C1 FUBBGQLTSCSAON-PBFPGSCMSA-N 0.000 description 2
- 229950004030 cefaloglycin Drugs 0.000 description 2
- HOKIDJSKDBPKTQ-GLXFQSAKSA-N cephalosporin C Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- CIPQGGYPCPIDBB-WPZCJLIBSA-N (6r)-3-methyl-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)C)C(O)=O)NC(=O)CC1=CC=CC=C1 CIPQGGYPCPIDBB-WPZCJLIBSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 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
- 239000004105 Penicillin G potassium Substances 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 102000006635 beta-lactamase Human genes 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CVWJDUUVFSVART-UHFFFAOYSA-N ethyl 2-amino-2-(4-hydroxyphenyl)acetate Chemical compound CCOC(=O)C(N)C1=CC=C(O)C=C1 CVWJDUUVFSVART-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000019368 penicillin G potassium Nutrition 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C12P35/00—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin
- C12P35/04—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin by acylation of the substituent in the 7 position
-
- 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
- C12P35/00—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin
- C12P35/02—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin by desacylation of the substituent in the 7 position
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (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)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT5448473 | 1973-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2460607A1 true DE2460607A1 (de) | 1975-06-26 |
Family
ID=11287332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742460607 Pending DE2460607A1 (de) | 1973-12-20 | 1974-12-20 | Enzymatische hydrolyse von cephalosporinen und enzymatische synthese von halbsynthetischen cephalosporinen |
Country Status (18)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2105988B1 (es) * | 1996-03-15 | 1998-07-01 | Antibioticos Sa | Procedimiento para purificar 7-sustituido-amino-desacetoxi-cefalosporinas mediante el empleo de membranas de filtracion. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5310156B2 (enrdf_load_stackoverflow) * | 1972-10-21 | 1978-04-11 | ||
| JPS52118A (en) * | 1975-06-23 | 1977-01-05 | Sony Corp | Still picture reproducing device |
-
1974
- 1974-11-28 IL IL46150A patent/IL46150A/xx unknown
- 1974-12-05 AU AU76089/74A patent/AU7608974A/en not_active Expired
- 1974-12-11 ZA ZA00747895A patent/ZA747895B/xx unknown
- 1974-12-12 FR FR7440980A patent/FR2255380B1/fr not_active Expired
- 1974-12-16 GB GB54336/74A patent/GB1480850A/en not_active Expired
- 1974-12-16 BE BE151538A patent/BE823392A/xx not_active IP Right Cessation
- 1974-12-17 YU YU03356/74A patent/YU335674A/xx unknown
- 1974-12-17 LU LU71506A patent/LU71506A1/xx unknown
- 1974-12-18 DD DD183150A patent/DD116833A5/xx unknown
- 1974-12-18 DK DK660374A patent/DK660374A/da not_active Application Discontinuation
- 1974-12-18 NL NL7416549A patent/NL7416549A/xx active Search and Examination
- 1974-12-19 NO NO744590A patent/NO744590L/no unknown
- 1974-12-19 HU HU74SA00002731A patent/HU172077B/hu unknown
- 1974-12-19 CA CA216,466A patent/CA1018091A/en not_active Expired
- 1974-12-19 SE SE7416077A patent/SE7416077L/xx unknown
- 1974-12-20 DE DE19742460607 patent/DE2460607A1/de active Pending
- 1974-12-20 CS CS748821A patent/CS209853B2/cs unknown
- 1974-12-20 JP JP49145850A patent/JPS5095486A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| YU335674A (en) | 1982-05-31 |
| SE7416077L (enrdf_load_stackoverflow) | 1975-06-23 |
| FR2255380A1 (enrdf_load_stackoverflow) | 1975-07-18 |
| LU71506A1 (enrdf_load_stackoverflow) | 1975-06-17 |
| NO744590L (enrdf_load_stackoverflow) | 1975-07-14 |
| BE823392A (fr) | 1975-04-16 |
| IL46150A0 (en) | 1975-02-10 |
| ZA747895B (en) | 1976-01-28 |
| GB1480850A (en) | 1977-07-27 |
| IL46150A (en) | 1979-07-25 |
| AU7608974A (en) | 1976-06-10 |
| JPS5095486A (enrdf_load_stackoverflow) | 1975-07-29 |
| DD116833A5 (enrdf_load_stackoverflow) | 1975-12-12 |
| CA1018091A (en) | 1977-09-27 |
| DK660374A (enrdf_load_stackoverflow) | 1975-08-25 |
| FR2255380B1 (enrdf_load_stackoverflow) | 1977-11-10 |
| CS209853B2 (en) | 1981-12-31 |
| NL7416549A (nl) | 1975-06-24 |
| HU172077B (hu) | 1978-05-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2343587A1 (de) | Verfahren zur herstellung von 2-ketol-gulonsaeure | |
| DE2360265A1 (de) | Verfahren zur herstellung von cephalosporinen | |
| DE2631048C3 (de) | Verfahren zur Herstellung von D-Phenylglycin | |
| DE2163791C2 (de) | Verfahren zur Herstellung von 7-Amino-3-methyl-3-cephem-4-carbonsäure und ihrer Ester | |
| RU2015166C1 (ru) | Способ получения 6-оксиникотиновой кислоты | |
| DE3027380C2 (enrdf_load_stackoverflow) | ||
| DE2417337A1 (de) | Verfahren zur biotechnischen herstellung von l-lysin und mutante zur durchfuehrung des verfahrens | |
| DE2757980C2 (enrdf_load_stackoverflow) | ||
| DE2460607A1 (de) | Enzymatische hydrolyse von cephalosporinen und enzymatische synthese von halbsynthetischen cephalosporinen | |
| DE2239321A1 (de) | Herstellung von cephalosporin c | |
| DE1945607C3 (de) | Verfahren zur Herstellung von p-Amino benzylpenicillin | |
| DE2723463A1 (de) | Verfahren zur herstellung von 7-amino- cephem-verbindungen unter verwendung von schimmelpilzen | |
| DE2407026A1 (de) | Verfahren zur erzeugung von hefezellen | |
| DE2331295A1 (de) | Verfahren zur herstellung von 7-aminodesacetoxy-cephalosporansaeure | |
| DE2407740C2 (de) | Herstellung einer als Protein-Nahrungsmittel oder Nahrungsmittelzusatz geeigneten Biomasse | |
| DE2050983C3 (de) | Verfahren zur Herstellung von alpha-Amino benzylpenicillin | |
| DE2332065C2 (de) | Verfahren zur Herstellung von Cephalosporinen sowie deren N-Alkoxycarbonyl- oder N-Arylcarbamoylderivaten | |
| DE2344006B2 (de) | Verfahren zur biotechnischen behandlung von epsilon-caprolactam enthaltenden abwaessern | |
| DE2533820A1 (de) | Verfahren zur deacylierung von penicillintetrazolen | |
| CH616165A5 (en) | Process for converting a 3-acyloxymethylceph-3-em-4-carboxylic acid into a 3-hydroxymethylceph-3-em-4-carboxylic acid. | |
| DE2163792A1 (de) | Verfahren zur Herstellung von Amino Penicillinen | |
| DE2157970C3 (de) | Verfahren zur Herstellung von 6-Aminopenicillansäure durch Spaltung von Penicillin G mittels trägergebundener Penicillinacylase | |
| DE2054310C3 (de) | Verfahren zur Herstellung von (-)-(cis-1 ^-EpoxypropyO-phosphonsaure | |
| AT234270B (de) | Verfahren zur Herstellung von α-Methylphenoxymethylpenicillin durch Fermentation | |
| DE1642726C (de) | Verfahren zur biotechnischen Herstellung von L-Threonin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHW | Rejection |