GB1347665A - Process for the production of cephalexin - Google Patents
Process for the production of cephalexinInfo
- Publication number
- GB1347665A GB1347665A GB3858772A GB3858772A GB1347665A GB 1347665 A GB1347665 A GB 1347665A GB 3858772 A GB3858772 A GB 3858772A GB 3858772 A GB3858772 A GB 3858772A GB 1347665 A GB1347665 A GB 1347665A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenylglycine
- enzyme
- cellulose
- enzyme preparations
- nrrl
- 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
- 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 title abstract 4
- 229940106164 cephalexin Drugs 0.000 title abstract 3
- 229940079919 digestives enzyme preparation Drugs 0.000 abstract 4
- 102000004190 Enzymes Human genes 0.000 abstract 3
- 108090000790 Enzymes Proteins 0.000 abstract 3
- 229940088598 enzyme Drugs 0.000 abstract 3
- 244000005700 microbiome Species 0.000 abstract 3
- 241000590020 Achromobacter Species 0.000 abstract 2
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 abstract 2
- 241000607598 Vibrio Species 0.000 abstract 2
- 230000001580 bacterial effect Effects 0.000 abstract 2
- 235000010633 broth Nutrition 0.000 abstract 2
- 239000001913 cellulose Substances 0.000 abstract 2
- 229920002678 cellulose Polymers 0.000 abstract 2
- 239000004927 clay Substances 0.000 abstract 2
- KIYRSYYOVDHSPG-SSDOTTSWSA-N (2r)-2-amino-2-phenylacetamide Chemical compound NC(=O)[C@H](N)C1=CC=CC=C1 KIYRSYYOVDHSPG-SSDOTTSWSA-N 0.000 abstract 1
- LJXOMNKURQBXLP-SECBINFHSA-N 2-[[(2r)-2-azaniumyl-2-phenylacetyl]amino]acetate Chemical compound OC(=O)CNC(=O)[C@H](N)C1=CC=CC=C1 LJXOMNKURQBXLP-SECBINFHSA-N 0.000 abstract 1
- 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 abstract 1
- 241000588986 Alcaligenes Species 0.000 abstract 1
- 241000588813 Alcaligenes faecalis Species 0.000 abstract 1
- 239000005995 Aluminium silicate Substances 0.000 abstract 1
- 241000193830 Bacillus <bacterium> Species 0.000 abstract 1
- 241000194107 Bacillus megaterium Species 0.000 abstract 1
- GUBGYTABKSRVRQ-WFVLMXAXSA-N DEAE-cellulose Chemical compound OC1C(O)C(O)C(CO)O[C@H]1O[C@@H]1C(CO)OC(O)C(O)C1O GUBGYTABKSRVRQ-WFVLMXAXSA-N 0.000 abstract 1
- 229920002307 Dextran Polymers 0.000 abstract 1
- 241000589565 Flavobacterium Species 0.000 abstract 1
- 241000589580 Flavobacterium aquatile Species 0.000 abstract 1
- 239000005909 Kieselgur Substances 0.000 abstract 1
- 241000736107 Novosphingobium capsulatum Species 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 229940005347 alcaligenes faecalis Drugs 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 235000012211 aluminium silicate Nutrition 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 239000001506 calcium phosphate Substances 0.000 abstract 1
- 229910000389 calcium phosphate Inorganic materials 0.000 abstract 1
- 235000011010 calcium phosphates Nutrition 0.000 abstract 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 239000000284 extract Substances 0.000 abstract 1
- 229910052588 hydroxylapatite Inorganic materials 0.000 abstract 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 abstract 1
- BHFLUDRTVIDDOR-MRVPVSSYSA-N methyl (2r)-2-amino-2-phenylacetate Chemical group COC(=O)[C@H](N)C1=CC=CC=C1 BHFLUDRTVIDDOR-MRVPVSSYSA-N 0.000 abstract 1
- 230000000813 microbial effect Effects 0.000 abstract 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000007790 solid phase Substances 0.000 abstract 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 abstract 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
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)
Abstract
1347665 Preparation of cephalexin TOYO JOZO KK 18 Aug 1972 [20 Aug 1971 14 Jan 1972] 38587/72 Heading C2A Cephalexin (7 - (D - α - aminophenylacetamido) - desacetoxy cephalosporanic acid) is prepared by reacting 7-aminodesacetoxy-cephalosporanic acid with D-phenylglycine or a reactive derivative thereof such as D-phenylglycine methyl or ethyl ester, D-phenylglycine amide, and D-phenylglycyl-glycine, -leucine or -alanine, in an aqueous medium in the presence of acylating enzyme derived from a microorganism selected from the genera Alcaligenes, Achromobacter, Flavobacterium, Bacillus and Beneckea such as Alcaligenes faecalis ATCC 8750, Achromobacter Nov. Sp. B-402-2 NRRL B-5393, Flavobacterium aquatile NRRL B-5394, Bacillus megaterium NRRL B-5385, Beneckea hiperoptica ATCC 15803, Flavobacterium capsulatum ATCC 14666. The acylation may be carried out batchwise or in a column, at a temperature of 20-45‹ C., at a pH of 5À5-7À5, for 0À5 to 3 hours, with a 2-20 molar excess of the D-phenylglycine reaction component, referred to the 7-aminoacetocy-cephalosporanic acid. The acylating enzyme preparations may be in the form of culture broths, bacterial cells, treated bacterial cells, enzyme extracts, solid phase enzyme preparations or insoluble enzyme preparations of the micro-organisms. Insolubilized enzyme preparations comprise a culture broth of the micro-organism, microbial cells thereof or enzyme prepared therefrom, absorbed on a solid carrier such as diatomaceous earth, acid clay, active clay, alumina, kaolin, calcium phosphate, hydroxy apatite, CM - cellulose, DEAE-cellulose, TEAE-cellulose or carboxymethyl cross-linked dextran.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP46063715A JPS5231436B2 (en) | 1971-08-20 | 1971-08-20 | |
| JP640772A JPS552958B2 (en) | 1972-01-14 | 1972-01-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1347665A true GB1347665A (en) | 1974-02-20 |
Family
ID=26340537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3858772A Expired GB1347665A (en) | 1971-08-20 | 1972-08-18 | Process for the production of cephalexin |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT324548B (en) |
| AU (1) | AU445437B2 (en) |
| BE (1) | BE787793A (en) |
| CA (1) | CA986440A (en) |
| CH (1) | CH588496A5 (en) |
| DD (1) | DD101166A5 (en) |
| DE (1) | DE2241091B2 (en) |
| FR (1) | FR2150380B1 (en) |
| GB (1) | GB1347665A (en) |
| HU (1) | HU164997B (en) |
| NL (1) | NL7211406A (en) |
| SE (1) | SE404928B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5231035B2 (en) * | 1972-08-22 | 1977-08-12 | ||
| FR2440402B1 (en) * | 1978-10-30 | 1981-08-14 | Inst Nat Rech Chimique | METHOD FOR IMMOBILIZING MICRO-ORGANISMS AND APPLICATIONS THEREOF |
| IT1274658B (en) * | 1995-02-28 | 1997-07-18 | Acs Dobfar Spa | IMPROVED ENZYMATIC PROCEDURE FOR THE PRODUCTION OF PENICILLINS AND CEPHALOSPORINS |
-
1972
- 1972-08-18 HU HUTO000884 patent/HU164997B/hu unknown
- 1972-08-18 CA CA150,260A patent/CA986440A/en not_active Expired
- 1972-08-18 GB GB3858772A patent/GB1347665A/en not_active Expired
- 1972-08-18 SE SE1072172A patent/SE404928B/en unknown
- 1972-08-18 FR FR7229647A patent/FR2150380B1/fr not_active Expired
- 1972-08-19 CH CH1231972A patent/CH588496A5/xx not_active IP Right Cessation
- 1972-08-21 AT AT719272A patent/AT324548B/en not_active IP Right Cessation
- 1972-08-21 DE DE19722241091 patent/DE2241091B2/en active Granted
- 1972-08-21 NL NL7211406A patent/NL7211406A/xx not_active Application Discontinuation
- 1972-08-21 AU AU45781/72A patent/AU445437B2/en not_active Expired
- 1972-08-21 BE BE787793A patent/BE787793A/en unknown
- 1972-08-21 DD DD16516072A patent/DD101166A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE404928B (en) | 1978-11-06 |
| FR2150380B1 (en) | 1974-10-04 |
| BE787793A (en) | 1972-12-18 |
| FR2150380A1 (en) | 1973-04-06 |
| DE2241091A1 (en) | 1973-03-15 |
| CA986440A (en) | 1976-03-30 |
| AU445437B2 (en) | 1974-02-21 |
| CH588496A5 (en) | 1977-06-15 |
| HU164997B (en) | 1974-05-28 |
| AT324548B (en) | 1975-09-10 |
| NL7211406A (en) | 1973-02-22 |
| DE2241091B2 (en) | 1976-02-05 |
| DD101166A5 (en) | 1973-10-20 |
| AU4578172A (en) | 1974-02-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |