JPS5982097A - 固定化酵素法による６−アミノペニシラン酸の改良製造法 - Google Patents
固定化酵素法による６−アミノペニシラン酸の改良製造法Info
- Publication number
- JPS5982097A JPS5982097A JP18919482A JP18919482A JPS5982097A JP S5982097 A JPS5982097 A JP S5982097A JP 18919482 A JP18919482 A JP 18919482A JP 18919482 A JP18919482 A JP 18919482A JP S5982097 A JPS5982097 A JP S5982097A
- Authority
- JP
- Japan
- Prior art keywords
- penicillin
- solution
- aqueous
- immobilized
- apa
- 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.)
- Granted
Links
- 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 title claims abstract description 36
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims description 57
- 108010093096 Immobilized Enzymes Proteins 0.000 title description 17
- 230000008569 process Effects 0.000 title 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 abstract description 34
- 108010073038 Penicillin Amidase Proteins 0.000 claims abstract description 33
- 239000000243 solution Substances 0.000 claims abstract description 30
- 239000007864 aqueous solution Substances 0.000 claims abstract description 27
- 238000000855 fermentation Methods 0.000 claims abstract description 15
- 230000004151 fermentation Effects 0.000 claims abstract description 15
- 239000006286 aqueous extract Substances 0.000 claims abstract description 14
- 238000000108 ultra-filtration Methods 0.000 claims abstract description 13
- 239000012736 aqueous medium Substances 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 238000000605 extraction Methods 0.000 claims abstract description 4
- 235000019371 penicillin G benzathine Nutrition 0.000 claims abstract 11
- 229940056360 penicillin g Drugs 0.000 claims abstract 11
- 238000004519 manufacturing process Methods 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 2
- 230000002255 enzymatic effect Effects 0.000 abstract description 4
- 239000012528 membrane Substances 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- 102000004190 Enzymes Human genes 0.000 description 17
- 108090000790 Enzymes Proteins 0.000 description 17
- 229930182555 Penicillin Natural products 0.000 description 11
- 229940049954 penicillin Drugs 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000872 buffer Substances 0.000 description 8
- 238000005947 deacylation reaction Methods 0.000 description 7
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 5
- 230000020176 deacylation Effects 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 239000008363 phosphate buffer Substances 0.000 description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 238000006911 enzymatic reaction Methods 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 229920002239 polyacrylonitrile Polymers 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 108700023418 Amidases Proteins 0.000 description 3
- 241000193830 Bacillus <bacterium> Species 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- 102000005922 amidase Human genes 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- DMGLDYFGHJWMJJ-UHFFFAOYSA-N 3-amino-5-(3-aminoanilino)-6-chloro-n-(diaminomethylidene)pyrazine-2-carboxamide Chemical compound N1=C(N)C(C(=O)N=C(N)N)=NC(Cl)=C1NC1=CC=CC(N)=C1 DMGLDYFGHJWMJJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 241000607720 Serratia Species 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000012510 hollow fiber Substances 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- -1 lithium aluminum hydride Chemical compound 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- DPEYHNFHDIXMNV-UHFFFAOYSA-N (9-amino-3-bicyclo[3.3.1]nonanyl)-(4-benzyl-5-methyl-1,4-diazepan-1-yl)methanone dihydrochloride Chemical compound Cl.Cl.CC1CCN(CCN1Cc1ccccc1)C(=O)C1CC2CCCC(C1)C2N DPEYHNFHDIXMNV-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- MTPJEFOSTIKRSS-UHFFFAOYSA-N 3-(dimethylamino)propanenitrile Chemical compound CN(C)CCC#N MTPJEFOSTIKRSS-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241000187844 Actinoplanes Species 0.000 description 1
- 241000194107 Bacillus megaterium Species 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 241000006479 Cyme Species 0.000 description 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 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 241000588698 Erwinia Species 0.000 description 1
- 229920001917 Ficoll Polymers 0.000 description 1
- 241000589565 Flavobacterium Species 0.000 description 1
- 101000976610 Homo sapiens Zinc finger protein 410 Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000191948 Kocuria rosea Species 0.000 description 1
- 241000192041 Micrococcus Species 0.000 description 1
- 241000187708 Micromonospora Species 0.000 description 1
- 241000187654 Nocardia Species 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N 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
- 102100023547 Zinc finger protein 410 Human genes 0.000 description 1
- 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 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical compound ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 description 1
- OHVFADVNPBHPRC-UHFFFAOYSA-L dipotassium acetic acid carbonate Chemical compound C([O-])([O-])=O.[K+].C(C)(=O)O.[K+] OHVFADVNPBHPRC-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000012487 in-house method Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000000203 mixture 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
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18919482A JPS5982097A (ja) | 1982-10-29 | 1982-10-29 | 固定化酵素法による６−アミノペニシラン酸の改良製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18919482A JPS5982097A (ja) | 1982-10-29 | 1982-10-29 | 固定化酵素法による６−アミノペニシラン酸の改良製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5982097A true JPS5982097A (ja) | 1984-05-11 |
| JPH0154999B2 JPH0154999B2 (enrdf_load_stackoverflow) | 1989-11-21 |
Family
ID=16237086
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18919482A Granted JPS5982097A (ja) | 1982-10-29 | 1982-10-29 | 固定化酵素法による６−アミノペニシラン酸の改良製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5982097A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5500352A (en) * | 1993-03-24 | 1996-03-19 | Sepracor, Inc. | Membrane filtration process for 6-aminopenicillanic acid |
| WO1997035029A1 (es) * | 1996-03-15 | 1997-09-25 | Antibioticos, S.A. | Procedimiento alternativo para la obtencion del acido 6-amino penicilanico (6-apa) |
| ES2105988A1 (es) * | 1996-03-15 | 1997-10-16 | Antibioticos Sa | Procedimiento para purificar 7-sustituido-amino-desacetoxi-cefalosporinas mediante el empleo de membranas de filtracion. |
-
1982
- 1982-10-29 JP JP18919482A patent/JPS5982097A/ja active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5500352A (en) * | 1993-03-24 | 1996-03-19 | Sepracor, Inc. | Membrane filtration process for 6-aminopenicillanic acid |
| US5521068A (en) * | 1993-03-24 | 1996-05-28 | Sepracor, Inc. | Process for 7-aminodesacetoxycephalosporanic acid |
| WO1997035029A1 (es) * | 1996-03-15 | 1997-09-25 | Antibioticos, S.A. | Procedimiento alternativo para la obtencion del acido 6-amino penicilanico (6-apa) |
| ES2105988A1 (es) * | 1996-03-15 | 1997-10-16 | Antibioticos Sa | Procedimiento para purificar 7-sustituido-amino-desacetoxi-cefalosporinas mediante el empleo de membranas de filtracion. |
| US6110699A (en) * | 1996-03-15 | 2000-08-29 | Antibioticos, S.A. | Process for producing 6-amino-penicillanic acid and phenylacetic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0154999B2 (enrdf_load_stackoverflow) | 1989-11-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2252699B1 (en) | Production of galactooligosaccharides by Bullera singularis and Saccharomyces sp. | |
| AU694176B2 (en) | Novel process for the isolation of clavulanic acid and of pharmaceutically acceptable salts thereof from the fermentation broth of streptomyces sp. p 6621 ferm p 2804 | |
| JPS5982097A (ja) | 固定化酵素法による６−アミノペニシラン酸の改良製造法 | |
| JP2002520066A (ja) | 固定化微生物によるマンニトールの製造方法 | |
| US3821081A (en) | Process for producing 7-amino desacetoxy cephalosporanic acid | |
| US4113566A (en) | Process for preparing 6-aminopenicillanic acid | |
| US3736230A (en) | Process for producing 6-amino-penicillanic acid | |
| AU603827B2 (en) | Novel preparation | |
| US5521068A (en) | Process for 7-aminodesacetoxycephalosporanic acid | |
| CN1045008C (zh) | 用黄青霉支顶孢菌生产头孢菌素c的方法 | |
| CN108220351B (zh) | 一种生物酶法制备L-精氨酸-α-酮戊二酸的方法 | |
| US3589982A (en) | Production of l-asparaginase | |
| JPH09154589A (ja) | エリスリトールの製造方法 | |
| GB2108128A (en) | Production of aspartase | |
| JPS63207400A (ja) | 廃糖蜜の脱色方法 | |
| JPH02207796A (ja) | 酵素を用いたガラクトオリゴ糖の製造法 | |
| JP2655618B2 (ja) | 微生物凝集剤ｎｏｃ―１の製造方法 | |
| CN100334221C (zh) | 一种直接法细胞酶反应生产丙烯酰胺水溶液的方法 | |
| US5015579A (en) | Production of (-)trans-2,3-epoxysuccinic acid by fermentation | |
| JP2884119B2 (ja) | ベンゼンジカルボン酸モノエステルまたはその誘導体の製造方法 | |
| KR800000422B1 (ko) | 고정화 포도당 산화효소의 제조방법 | |
| DE2212276C3 (de) | Verfahren zur Herstellung von 7-Aminodesacetoxy-cephalospora nsäure | |
| JPH01317391A (ja) | Ｄ―β―ヒドロキシアミノ酸を取得する方法 | |
| EP0114630A2 (de) | Permeabilisiertes Schimmelpilzmycel mit intaktem immobilisiertem Glucoseoxidase-Katalasesystem sowie dessen Herstellung und Anwendung | |
| CN117106844A (zh) | 发酵法合成苯氧乙酰胺基青霉素钾盐的方法 |