DE2241091C3 - - Google Patents
Info
- Publication number
- DE2241091C3 DE2241091C3 DE19722241091 DE2241091A DE2241091C3 DE 2241091 C3 DE2241091 C3 DE 2241091C3 DE 19722241091 DE19722241091 DE 19722241091 DE 2241091 A DE2241091 A DE 2241091A DE 2241091 C3 DE2241091 C3 DE 2241091C3
- Authority
- DE
- Germany
- Prior art keywords
- enzyme
- cephalexin
- cells
- adca
- hours
- 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
- 108090000790 Enzymes Proteins 0.000 claims description 36
- 102000004190 Enzymes Human genes 0.000 claims description 36
- NVIAYEIXYQCDAN-CLZZGJSISA-N 7β-aminodeacetoxycephalosporanic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](N)[C@@H]12 NVIAYEIXYQCDAN-CLZZGJSISA-N 0.000 claims description 30
- 244000005700 microbiome Species 0.000 claims description 24
- 241000590020 Achromobacter Species 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 125000004494 ethyl ester group Chemical group 0.000 claims description 7
- 241000607598 Vibrio Species 0.000 claims description 4
- 210000004027 cells Anatomy 0.000 description 42
- AVGYWQBCYZHHPN-CYJZLJNKSA-N cephalexin monohydrate Chemical compound O.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 AVGYWQBCYZHHPN-CYJZLJNKSA-N 0.000 description 39
- 229940106164 Cephalexin Drugs 0.000 description 38
- 229960003525 cefalexin Drugs 0.000 description 38
- 229940088598 Enzyme Drugs 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000000969 carrier Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000002609 media Substances 0.000 description 14
- 239000004793 Polystyrene Substances 0.000 description 13
- 238000005917 acylation reaction Methods 0.000 description 13
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 12
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- 238000004519 manufacturing process Methods 0.000 description 10
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- 239000002253 acid Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
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- -1 Amino - phenylacetamido Chemical class 0.000 description 6
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- 239000003957 anion exchange resin Substances 0.000 description 4
- 229940079919 digestives Enzyme preparations Drugs 0.000 description 4
- 238000000855 fermentation Methods 0.000 description 4
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- SIKJAQJRHWYJAI-UHFFFAOYSA-N indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- BHFLUDRTVIDDOR-MRVPVSSYSA-N methyl (2R)-2-amino-2-phenylacetate Chemical compound COC(=O)[C@H](N)C1=CC=CC=C1 BHFLUDRTVIDDOR-MRVPVSSYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- BFSVOASYOCHEOV-UHFFFAOYSA-N Diethylethanolamine Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 3
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- DTHMTBUWTGVEFG-DDWIOCJRSA-N methyl (2R)-2-amino-2-phenylacetate;hydrochloride Chemical compound Cl.COC(=O)[C@H](N)C1=CC=CC=C1 DTHMTBUWTGVEFG-DDWIOCJRSA-N 0.000 description 3
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- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
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- 239000005909 Kieselgur Substances 0.000 description 2
- GUBGYTABKSRVRQ-YOLKTULGSA-N Maltose Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)O[C@H]1CO)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 GUBGYTABKSRVRQ-YOLKTULGSA-N 0.000 description 2
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- 238000010521 absorption reaction Methods 0.000 description 2
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- 150000003863 ammonium salts Chemical class 0.000 description 2
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- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
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- 239000004927 clay Substances 0.000 description 2
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- 238000004108 freeze drying Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
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- 239000006166 lysate Substances 0.000 description 2
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- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
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- 239000008363 phosphate buffer Substances 0.000 description 2
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- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- ZGUNAGUHMKGQNY-UHFFFAOYSA-N α-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 2
- IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6R)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 description 1
- FURUSGMMMFSWDW-UHFFFAOYSA-N 2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]acetic acid Chemical class CC(C)(C)OC(=O)NC1=CC=CC=C1CC(O)=O FURUSGMMMFSWDW-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K 2qpq Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- PZZYQPZGQPZBDN-UHFFFAOYSA-N Aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000194107 Bacillus megaterium Species 0.000 description 1
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- 229940105657 CATALASE Drugs 0.000 description 1
- 229960001927 Cetylpyridinium Chloride Drugs 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
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N D-sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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- CDAISMWEOUEBRE-GPIVLXJGSA-N Inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
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- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
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- 239000006285 cell suspension Substances 0.000 description 1
- HOKIDJSKDBPKTQ-GLXFQSAKSA-M cephalosporin C(1-) Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H]([NH3+])C([O-])=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-M 0.000 description 1
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- 238000005538 encapsulation Methods 0.000 description 1
- VWKGPFHYXWGWEI-SECBINFHSA-N ethyl (2R)-2-amino-2-phenylacetate Chemical compound CCOC(=O)[C@H](N)C1=CC=CC=C1 VWKGPFHYXWGWEI-SECBINFHSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 239000001963 growth media Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000009114 investigational therapy Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229960000274 lysozyme Drugs 0.000 description 1
- 239000004325 lysozyme Substances 0.000 description 1
- 235000010335 lysozyme Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
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- 235000013379 molasses Nutrition 0.000 description 1
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- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 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 description 1
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- 108040003878 secondary active transmembrane transporter activity proteins Proteins 0.000 description 1
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- 239000011780 sodium chloride Substances 0.000 description 1
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Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6371571 | 1971-08-20 | ||
| JP46063715A JPS5231436B2 (es) | 1971-08-20 | 1971-08-20 | |
| JP640772A JPS552958B2 (es) | 1972-01-14 | 1972-01-14 | |
| JP640772 | 1972-01-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2241091A1 DE2241091A1 (de) | 1973-03-15 |
| DE2241091B2 DE2241091B2 (de) | 1976-02-05 |
| DE2241091C3 true DE2241091C3 (es) | 1976-10-07 |
Family
ID=26340537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722241091 Granted DE2241091B2 (de) | 1971-08-20 | 1972-08-21 | Verfahren zur herstellung von 7- (d-alpha-aminophenylacetoamido)-desace- toxy-cephalosporansaeure |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT324548B (es) |
| AU (1) | AU445437B2 (es) |
| BE (1) | BE787793A (es) |
| CA (1) | CA986440A (es) |
| CH (1) | CH588496A5 (es) |
| DD (1) | DD101166A5 (es) |
| DE (1) | DE2241091B2 (es) |
| FR (1) | FR2150380B1 (es) |
| GB (1) | GB1347665A (es) |
| HU (1) | HU164997B (es) |
| NL (1) | NL7211406A (es) |
| SE (1) | SE404928B (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5231035B2 (es) * | 1972-08-22 | 1977-08-12 | ||
| FR2440402B1 (fr) * | 1978-10-30 | 1981-08-14 | Inst Nat Rech Chimique | Procede d'immobilisation de micro-organismes et ses applications |
| IT1274658B (it) * | 1995-02-28 | 1997-07-18 | Acs Dobfar Spa | Procedimento enzimatico migliorato per la produzione di penicilline e cefalosporine |
-
1972
- 1972-08-18 GB GB3858772A patent/GB1347665A/en not_active Expired
- 1972-08-18 CA CA150,260A patent/CA986440A/en not_active Expired
- 1972-08-18 FR FR7229647A patent/FR2150380B1/fr not_active Expired
- 1972-08-18 HU HUTO000884 patent/HU164997B/hu unknown
- 1972-08-18 SE SE1072172A patent/SE404928B/xx unknown
- 1972-08-19 CH CH1231972A patent/CH588496A5/xx not_active IP Right Cessation
- 1972-08-21 AT AT719272A patent/AT324548B/de not_active IP Right Cessation
- 1972-08-21 BE BE787793A patent/BE787793A/xx unknown
- 1972-08-21 DE DE19722241091 patent/DE2241091B2/de active Granted
- 1972-08-21 NL NL7211406A patent/NL7211406A/xx not_active Application Discontinuation
- 1972-08-21 DD DD16516072A patent/DD101166A5/xx unknown
- 1972-08-21 AU AU45781/72A patent/AU445437B2/en not_active Expired
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