HU176598B - Process for preparing 6-amino-penicillanic with the enzymatic deacylation of penicillines - Google Patents
Process for preparing 6-amino-penicillanic with the enzymatic deacylation of penicillines Download PDFInfo
- Publication number
- HU176598B HU176598B HU77PI605A HUPI000605A HU176598B HU 176598 B HU176598 B HU 176598B HU 77PI605 A HU77PI605 A HU 77PI605A HU PI000605 A HUPI000605 A HU PI000605A HU 176598 B HU176598 B HU 176598B
- Authority
- HU
- Hungary
- Prior art keywords
- penicillin
- catalyst
- bed
- conversion
- immobilized
- Prior art date
Links
- 230000002255 enzymatic effect Effects 0.000 title claims description 4
- 230000020176 deacylation Effects 0.000 title description 7
- 238000005947 deacylation reaction Methods 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims description 40
- 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 35
- 229930182555 Penicillin Natural products 0.000 claims description 29
- 229940049954 penicillin Drugs 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 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 15
- 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 15
- 108010073038 Penicillin Amidase Proteins 0.000 claims description 15
- 108090000790 Enzymes Proteins 0.000 claims description 10
- 102000004190 Enzymes Human genes 0.000 claims description 10
- 229940056360 penicillin g Drugs 0.000 claims description 6
- 150000002960 penicillins Chemical class 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 241000588769 Proteus <enterobacteria> Species 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- 210000004027 cell Anatomy 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 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 7
- 241000588777 Providencia rettgeri Species 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- 244000005700 microbiome Species 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 210000001822 immobilized cell Anatomy 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000901842 Escherichia coli W Species 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 229930195708 Penicillin V Natural products 0.000 description 2
- AZCVBVRUYHKWHU-MBNYWOFBSA-N Penicillin X Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=C(O)C=C1 AZCVBVRUYHKWHU-MBNYWOFBSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229940056367 penicillin v Drugs 0.000 description 2
- 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 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000192041 Micrococcus Species 0.000 description 1
- 241000187654 Nocardia Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000034809 Product contamination Diseases 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 238000002306 biochemical method Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- SHFGJEQAOUMGJM-UHFFFAOYSA-N dialuminum dipotassium disodium dioxosilane iron(3+) oxocalcium oxomagnesium oxygen(2-) Chemical compound [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[Na+].[Na+].[Al+3].[Al+3].[K+].[K+].[Fe+3].[Fe+3].O=[Mg].O=[Ca].O=[Si]=O SHFGJEQAOUMGJM-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- AZCVBVRUYHKWHU-UHFFFAOYSA-N penicillin X Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)CC1=CC=C(O)C=C1 AZCVBVRUYHKWHU-UHFFFAOYSA-N 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000019814 powdered cellulose Nutrition 0.000 description 1
- 229920003124 powdered cellulose Polymers 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/42—Compounds with a free primary amino radical attached in position 6
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/873—Proteus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Cephalosporin Compounds (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/745,212 US4113566A (en) | 1976-11-26 | 1976-11-26 | Process for preparing 6-aminopenicillanic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU176598B true HU176598B (en) | 1981-03-28 |
Family
ID=24995717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU77PI605A HU176598B (en) | 1976-11-26 | 1977-11-25 | Process for preparing 6-amino-penicillanic with the enzymatic deacylation of penicillines |
Country Status (29)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59110763U (ja) * | 1983-01-18 | 1984-07-26 | 日産自動車株式会社 | パ−キングブレ−キ力伝達装置 |
| ES2135446T3 (es) * | 1992-04-24 | 1999-11-01 | Lilly Co Eli | Procedimiento para la preparacion de cefalosporinas. |
| US6107067A (en) * | 1998-07-06 | 2000-08-22 | W.R. Grace & Co.-Conn. | Porous, non-macroporous, inorganic oxide carrier body for immobilizing microorganisms for bioremediation |
| KR101760957B1 (ko) | 2009-05-20 | 2017-07-24 | 질레코 인코포레이티드 | 바이오처리방법 |
| ES2429912B1 (es) * | 2012-05-14 | 2014-11-26 | Universidad Autónoma de Madrid | Polipéptido termoestable con actividad penicilina acilasa, variantes del mismo y sus aplicaciones |
| CN105254520B (zh) * | 2015-10-12 | 2017-07-07 | 国药集团威奇达药业有限公司 | 酶法合成阿莫西林结晶母液中d‑对羟基苯甘氨酸的回收方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3239427A (en) * | 1959-10-12 | 1966-03-08 | Pfizer & Co C | Production of 6-aminopenicillanic acid |
| US3817832A (en) * | 1970-11-09 | 1974-06-18 | Standard Brands Inc | Process for isomerizing glucose to fructose |
| US3694314A (en) * | 1970-11-09 | 1972-09-26 | Standard Brands Inc | Process for isomerizing glucose to fructose |
| IL39158A (en) | 1971-04-28 | 1977-08-31 | Snam Progetti | Enzymatic scission and synthesis of penicillins and cephalosporins |
| BE791748A (fr) * | 1971-11-23 | 1973-05-22 | Bayer Ag | Procede de production d'acide 6-aminopenicillanique par ruptureenzymatique de penicillines |
| DE2215539C2 (de) * | 1972-03-30 | 1984-08-02 | Bayer Ag, 5090 Leverkusen | Neue wasserunlösliche Enzym-, insbesondere Penicillinacylase-oder Enzyminhibitor-Präparate |
| GB1400468A (en) * | 1972-07-22 | 1975-07-16 | Beecham Group Ltd | Enzyme preparation and use thereof |
| JPS5317674B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-05-30 | 1978-06-09 | ||
| CH597237A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-01-31 | 1978-03-31 | Biochemie Gmbh | |
| US3905868A (en) * | 1974-12-04 | 1975-09-16 | Pfizer | Enzymatic deacylation of benzyl- and phenoxymethylpenicillin tetrazoles |
-
1976
- 1976-11-26 US US05/745,212 patent/US4113566A/en not_active Expired - Lifetime
-
1977
- 1977-10-25 SE SE7712006A patent/SE434157B/xx not_active IP Right Cessation
- 1977-11-01 IN IN360/DEC/77A patent/IN147632B/en unknown
- 1977-11-03 PH PH20397A patent/PH12580A/en unknown
- 1977-11-07 MX MX776530U patent/MX4233E/es unknown
- 1977-11-09 YU YU02679/77A patent/YU267977A/xx unknown
- 1977-11-15 IT IT51812/77A patent/IT1092206B/it active
- 1977-11-15 ES ES464141A patent/ES464141A1/es not_active Expired
- 1977-11-16 AR AR269997A patent/AR218273A1/es active
- 1977-11-17 RO RO7792151A patent/RO73018A/ro unknown
- 1977-11-17 BG BG037816A patent/BG32859A3/xx unknown
- 1977-11-23 CS CS777745A patent/CS207715B2/cs unknown
- 1977-11-24 DE DE2752499A patent/DE2752499C2/de not_active Expired
- 1977-11-24 CA CA291,675A patent/CA1089383A/en not_active Expired
- 1977-11-25 PL PL1977202402A patent/PL109707B1/pl unknown
- 1977-11-25 FR FR7735615A patent/FR2372166A1/fr active Granted
- 1977-11-25 ZA ZA00777018A patent/ZA777018B/xx unknown
- 1977-11-25 GB GB49198/77A patent/GB1537640A/en not_active Expired
- 1977-11-25 LU LU78585A patent/LU78585A1/xx unknown
- 1977-11-25 DD DD7700202261A patent/DD133674A5/xx unknown
- 1977-11-25 JP JP14146477A patent/JPS5369888A/ja active Granted
- 1977-11-25 CH CH1450077A patent/CH625556A5/fr not_active IP Right Cessation
- 1977-11-25 IE IE2389/77A patent/IE45997B1/en not_active IP Right Cessation
- 1977-11-25 NL NLAANVRAGE7712999,A patent/NL171821C/xx not_active IP Right Cessation
- 1977-11-25 SU SU772545994A patent/SU719504A3/ru active
- 1977-11-25 HU HU77PI605A patent/HU176598B/hu unknown
- 1977-11-25 BE BE182929A patent/BE861207A/xx not_active IP Right Cessation
- 1977-11-25 AU AU30979/77A patent/AU500707B1/en not_active Expired
- 1977-11-25 DK DK524977A patent/DK144277C/da active
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