IL39158A - Enzymatic scission and synthesis of penicillins and cephalosporins - Google Patents
Enzymatic scission and synthesis of penicillins and cephalosporinsInfo
- Publication number
- IL39158A IL39158A IL39158A IL3915872A IL39158A IL 39158 A IL39158 A IL 39158A IL 39158 A IL39158 A IL 39158A IL 3915872 A IL3915872 A IL 3915872A IL 39158 A IL39158 A IL 39158A
- Authority
- IL
- Israel
- Prior art keywords
- filament
- substance
- enzyme
- reaction medium
- penicillins
- Prior art date
Links
- 229930182555 Penicillin Natural products 0.000 title claims abstract description 61
- 150000002960 penicillins Chemical class 0.000 title claims abstract description 40
- 229930186147 Cephalosporin Natural products 0.000 title claims abstract description 19
- 229940124587 cephalosporin Drugs 0.000 title claims abstract description 19
- 150000001780 cephalosporins Chemical class 0.000 title claims abstract description 19
- 230000002255 enzymatic effect Effects 0.000 title claims abstract description 11
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 10
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 8
- 238000010504 bond cleavage reaction Methods 0.000 title description 2
- 230000007017 scission Effects 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 69
- 108090000790 Enzymes Proteins 0.000 claims abstract description 60
- 102000004190 Enzymes Human genes 0.000 claims abstract description 60
- 239000000126 substance Substances 0.000 claims abstract description 39
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- 239000012429 reaction media Substances 0.000 claims abstract description 29
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 20
- 230000007062 hydrolysis Effects 0.000 claims abstract description 19
- 229920000642 polymer Polymers 0.000 claims abstract description 9
- -1 ampicillin Chemical class 0.000 claims abstract description 8
- 230000000717 retained effect Effects 0.000 claims abstract description 8
- 241000588724 Escherichia coli Species 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 230000000694 effects Effects 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 241000228212 Aspergillus Species 0.000 claims abstract description 4
- 241000235395 Mucor Species 0.000 claims abstract description 4
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims abstract description 4
- 229960000723 ampicillin Drugs 0.000 claims abstract description 4
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims abstract description 3
- 241000223600 Alternaria Species 0.000 claims abstract description 3
- 241000123650 Botrytis cinerea Species 0.000 claims abstract description 3
- 239000001856 Ethyl cellulose Substances 0.000 claims abstract description 3
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000004952 Polyamide Substances 0.000 claims abstract description 3
- 241000187747 Streptomyces Species 0.000 claims abstract description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 229920001577 copolymer Polymers 0.000 claims abstract description 3
- 229920001249 ethyl cellulose Polymers 0.000 claims abstract description 3
- 235000019325 ethyl cellulose Nutrition 0.000 claims abstract description 3
- 108700004370 poly-gamma-methylglutamate Proteins 0.000 claims abstract description 3
- 229920002647 polyamide Polymers 0.000 claims abstract description 3
- 229920001567 vinyl ester resin Polymers 0.000 claims abstract description 3
- 230000001580 bacterial effect Effects 0.000 claims abstract 3
- 230000002538 fungal effect Effects 0.000 claims abstract 3
- 241000588813 Alcaligenes faecalis Species 0.000 claims abstract 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims abstract 2
- 229940005347 alcaligenes faecalis Drugs 0.000 claims abstract 2
- 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 41
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 claims description 28
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 claims description 28
- 229940049954 penicillin Drugs 0.000 claims description 22
- 239000007864 aqueous solution Substances 0.000 claims description 20
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 claims description 11
- 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 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 7
- 239000000284 extract Substances 0.000 claims description 5
- 239000002243 precursor Substances 0.000 claims description 4
- 108010073038 Penicillin Amidase Proteins 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims description 2
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims description 2
- 241000186361 Actinobacteria <class> Species 0.000 claims description 2
- 241000588986 Alcaligenes Species 0.000 claims description 2
- 241000223218 Fusarium Species 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 241000228143 Penicillium Species 0.000 claims 2
- JGSARLDLIJGVTE-UHFFFAOYSA-N 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-UHFFFAOYSA-N 0.000 claims 1
- 241001158232 Bacillus magaterium Species 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical group [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 4
- 229920002284 Cellulose triacetate Polymers 0.000 abstract description 3
- 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 abstract description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract description 2
- 241000588915 Klebsiella aerogenes Species 0.000 abstract description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 abstract description 2
- 229920000098 polyolefin Polymers 0.000 abstract description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- 241000186046 Actinomyces Species 0.000 abstract 1
- 241000194107 Bacillus megaterium Species 0.000 abstract 1
- 238000002317 scanning near-field acoustic microscopy Methods 0.000 abstract 1
- 229940088598 enzyme Drugs 0.000 description 42
- 239000000243 solution Substances 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 229940056360 penicillin g Drugs 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 6
- 238000000855 fermentation Methods 0.000 description 6
- 230000004151 fermentation Effects 0.000 description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229940056367 penicillin v Drugs 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229930195708 Penicillin V Natural products 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 230000020176 deacylation Effects 0.000 description 4
- 238000005947 deacylation reaction Methods 0.000 description 4
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229960003424 phenylacetic acid Drugs 0.000 description 3
- 239000003279 phenylacetic acid Substances 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 108700023418 Amidases Proteins 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 102000005922 amidase Human genes 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- IYNDLOXRXUOGIU-LQDWTQKMSA-M benzylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 IYNDLOXRXUOGIU-LQDWTQKMSA-M 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- MAGPZHKLEZXLNU-UHFFFAOYSA-N mandelamide Chemical compound NC(=O)C(O)C1=CC=CC=C1 MAGPZHKLEZXLNU-UHFFFAOYSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 235000019371 penicillin G benzathine Nutrition 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-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
- 241000894006 Bacteria Species 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 101001091385 Homo sapiens Kallikrein-6 Proteins 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 102100034866 Kallikrein-6 Human genes 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 241000228150 Penicillium chrysogenum Species 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000012505 colouration Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000006862 enzymatic digestion Effects 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C12P35/02—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
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Cephalosporin Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2377771 | 1971-04-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL39158A0 IL39158A0 (en) | 1972-06-28 |
| IL39158A true IL39158A (en) | 1977-08-31 |
Family
ID=11209882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL39158A IL39158A (en) | 1971-04-28 | 1972-04-07 | Enzymatic scission and synthesis of penicillins and cephalosporins |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5413514B1 (en)) |
| AR (1) | AR192936A1 (en)) |
| AT (1) | AT318805B (en)) |
| BE (1) | BE782646A (en)) |
| BR (1) | BR7202723D0 (en)) |
| CH (2) | CH565181A5 (en)) |
| CS (1) | CS223812B2 (en)) |
| DD (1) | DD100721A5 (en)) |
| DE (1) | DE2221046A1 (en)) |
| EG (1) | EG10474A (en)) |
| ES (1) | ES402865A1 (en)) |
| FR (1) | FR2134530B1 (en)) |
| GB (1) | GB1348359A (en)) |
| HU (1) | HU168856B (en)) |
| IE (1) | IE36334B1 (en)) |
| IL (1) | IL39158A (en)) |
| LU (1) | LU65258A1 (en)) |
| NL (1) | NL7205609A (en)) |
| PL (1) | PL98632B1 (en)) |
| YU (3) | YU112572A (en)) |
| ZA (1) | ZA722837B (en)) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1492937A (en) * | 1973-12-28 | 1977-11-23 | Beecham Group Ltd | Enzyme complexes and their use |
| DE2409569C2 (de) * | 1974-02-28 | 1982-02-18 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von 7-Amino- Ω3-cephem-Derivaten |
| US4113566A (en) * | 1976-11-26 | 1978-09-12 | Pfizer Inc. | Process for preparing 6-aminopenicillanic acid |
| US4596777A (en) * | 1983-08-10 | 1986-06-24 | E. R. Squibb & Sons, Inc. | Process for preparing (3S)-3-[[[2-(protected or unprotected amino)-4-thiazolyl]acetyl]amino]-2-oxo-1-azetidinesulfonic acid and 4-substituted derivatives thereof |
| CZ69593A3 (en) * | 1992-04-24 | 1993-12-15 | Lilly Co Eli | Process for preparing cephalosporins |
| DE19646550A1 (de) * | 1996-10-31 | 1998-05-07 | Fzb Biotechnik Gmbh | Kombiniertes Verfahren zur lösungsmittelarmen Gewinnung von Produkten aus der biokatalytischen Spaltung von Penicillin- oder Cephalosporin G-Lösungen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE727506A (en)) * | 1968-02-15 | 1969-07-01 | ||
| ES365631A1 (es) * | 1968-04-05 | 1971-03-16 | Beecham Group Ltd | Un procedimiento para la preparacion de acido 6-aminopeni- cilanico. |
-
1972
- 1972-04-07 IL IL39158A patent/IL39158A/en unknown
- 1972-04-09 EG EG140/72A patent/EG10474A/xx active
- 1972-04-11 CS CS722414A patent/CS223812B2/cs unknown
- 1972-04-25 NL NL7205609A patent/NL7205609A/xx unknown
- 1972-04-26 FR FR7214799A patent/FR2134530B1/fr not_active Expired
- 1972-04-26 JP JP4215072A patent/JPS5413514B1/ja active Pending
- 1972-04-26 BE BE782646A patent/BE782646A/xx not_active IP Right Cessation
- 1972-04-26 AR AR241744A patent/AR192936A1/es active
- 1972-04-26 DD DD162592A patent/DD100721A5/xx unknown
- 1972-04-26 PL PL1972154991A patent/PL98632B1/pl unknown
- 1972-04-27 ES ES402865A patent/ES402865A1/es not_active Expired
- 1972-04-27 YU YU01125/72A patent/YU112572A/xx unknown
- 1972-04-27 IE IE561/72A patent/IE36334B1/xx unknown
- 1972-04-27 ZA ZA722837A patent/ZA722837B/xx unknown
- 1972-04-27 GB GB1972672A patent/GB1348359A/en not_active Expired
- 1972-04-27 BR BR2723/72A patent/BR7202723D0/pt unknown
- 1972-04-27 HU HUSA2349A patent/HU168856B/hu unknown
- 1972-04-27 LU LU65258D patent/LU65258A1/xx unknown
- 1972-04-28 CH CH440373A patent/CH565181A5/xx not_active IP Right Cessation
- 1972-04-28 DE DE19722221046 patent/DE2221046A1/de active Pending
- 1972-04-28 CH CH643472A patent/CH550822A/fr not_active IP Right Cessation
- 1972-04-28 AT AT377372A patent/AT318805B/de not_active IP Right Cessation
-
1979
- 1979-09-05 YU YU02166/79A patent/YU216679A/xx unknown
-
1980
- 1980-04-17 YU YU01061/80A patent/YU106180A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH565181A5 (en)) | 1975-08-15 |
| AT318805B (de) | 1974-11-25 |
| PL98632B1 (pl) | 1978-05-31 |
| EG10474A (en) | 1976-04-30 |
| DD100721A5 (en)) | 1973-10-05 |
| ES402865A1 (es) | 1976-02-01 |
| BE782646A (fr) | 1972-08-16 |
| YU216679A (en) | 1982-05-31 |
| DE2221046A1 (de) | 1973-11-15 |
| NL7205609A (en)) | 1972-10-31 |
| JPS5413514B1 (en)) | 1979-05-31 |
| AR192936A1 (es) | 1973-03-21 |
| YU106180A (en) | 1982-05-31 |
| BR7202723D0 (pt) | 1974-02-19 |
| ZA722837B (en) | 1973-02-28 |
| HU168856B (en)) | 1976-07-28 |
| FR2134530B1 (en)) | 1975-10-17 |
| IE36334B1 (en) | 1976-10-13 |
| IE36334L (en) | 1972-10-28 |
| LU65258A1 (en)) | 1972-07-14 |
| IL39158A0 (en) | 1972-06-28 |
| FR2134530A1 (en)) | 1972-12-08 |
| CH550822A (fr) | 1974-06-28 |
| GB1348359A (en) | 1974-03-13 |
| CS223812B2 (en) | 1983-11-25 |
| YU112572A (en) | 1982-02-28 |
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