JPS5840474B2 - 酵素反応により有機物質を少くとも１種類の他の有機物質に変換する酵素利用法 - Google Patents
酵素反応により有機物質を少くとも１種類の他の有機物質に変換する酵素利用法Info
- Publication number
- JPS5840474B2 JPS5840474B2 JP51061294A JP6129476A JPS5840474B2 JP S5840474 B2 JPS5840474 B2 JP S5840474B2 JP 51061294 A JP51061294 A JP 51061294A JP 6129476 A JP6129476 A JP 6129476A JP S5840474 B2 JPS5840474 B2 JP S5840474B2
- Authority
- JP
- Japan
- Prior art keywords
- enzyme
- complex
- enzyme complex
- reaction
- substance
- 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 title claims description 120
- 102000004190 Enzymes Human genes 0.000 title claims description 120
- 238000000034 method Methods 0.000 title claims description 21
- 239000000126 substance Substances 0.000 title claims description 18
- 238000006911 enzymatic reaction Methods 0.000 title claims description 13
- 239000012429 reaction media Substances 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 230000000694 effects Effects 0.000 claims description 13
- 229920000620 organic polymer Polymers 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 229940088598 enzyme Drugs 0.000 description 111
- 239000000243 solution Substances 0.000 description 19
- 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 17
- 239000008103 glucose Substances 0.000 description 17
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- 239000012736 aqueous medium Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 8
- 229920002472 Starch Polymers 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 239000008107 starch Substances 0.000 description 7
- 235000019698 starch Nutrition 0.000 description 7
- 229930091371 Fructose Natural products 0.000 description 6
- 239000005715 Fructose Substances 0.000 description 6
- 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 6
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 6
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 6
- 229920002401 polyacrylamide Polymers 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 102100026189 Beta-galactosidase Human genes 0.000 description 4
- 108010073178 Glucan 1,4-alpha-Glucosidase Proteins 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 108010059881 Lactase Proteins 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- 108700040099 Xylose isomerases Proteins 0.000 description 4
- 150000001540 azides Chemical class 0.000 description 4
- 108010005774 beta-Galactosidase Proteins 0.000 description 4
- 229940116108 lactase Drugs 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 229920002521 macromolecule Polymers 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 3
- 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 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229920003169 water-soluble polymer Polymers 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 102100022624 Glucoamylase Human genes 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 235000011148 calcium chloride Nutrition 0.000 description 2
- 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
- 238000005119 centrifugation Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229960001484 edetic acid Drugs 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 229930182830 galactose Natural products 0.000 description 2
- 230000003100 immobilizing effect Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000004584 polyacrylic acid Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QBYMCVQZZZQPHE-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetic acid;calcium Chemical compound [Ca].OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O QBYMCVQZZZQPHE-UHFFFAOYSA-N 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 108090000769 Isomerases Proteins 0.000 description 1
- 102000004195 Isomerases Human genes 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products 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-PICCSMPSSA-N 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004365 Protease Substances 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
- 239000002253 acid Substances 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 108090000637 alpha-Amylases Proteins 0.000 description 1
- 102000004139 alpha-Amylases Human genes 0.000 description 1
- 229940024171 alpha-amylase Drugs 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 229940025131 amylases Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 108010019077 beta-Amylase Proteins 0.000 description 1
- 108010051210 beta-Fructofuranosidase Proteins 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000010799 enzyme reaction rate Methods 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000021433 fructose syrup Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- 239000001573 invertase Substances 0.000 description 1
- 235000011073 invertase Nutrition 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 229920003176 water-insoluble polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier
- C12N11/10—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a carbohydrate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/59—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
- A61K47/60—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier
- C12N11/08—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer
- C12N11/082—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C12N11/087—Acrylic polymers
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier
- C12N11/08—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer
- C12N11/089—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K1/00—Glucose; Glucose-containing syrups
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K11/00—Fructose
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Molecular Biology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH696575A CH596313A5 (enExample) | 1975-05-30 | 1975-05-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51144787A JPS51144787A (en) | 1976-12-13 |
| JPS5840474B2 true JPS5840474B2 (ja) | 1983-09-06 |
Family
ID=4317814
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51061294A Expired JPS5840474B2 (ja) | 1975-05-30 | 1976-05-28 | 酵素反応により有機物質を少くとも１種類の他の有機物質に変換する酵素利用法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4088538A (enExample) |
| JP (1) | JPS5840474B2 (enExample) |
| CH (1) | CH596313A5 (enExample) |
| DE (1) | DE2624002C2 (enExample) |
| FR (1) | FR2312561A1 (enExample) |
| GB (1) | GB1554211A (enExample) |
Families Citing this family (88)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4780409A (en) * | 1985-05-02 | 1988-10-25 | Genetic Systems Corporation | Thermally induced phase separation immunoassay |
| US5206344A (en) * | 1985-06-26 | 1993-04-27 | Cetus Oncology Corporation | Interleukin-2 muteins and polymer conjugation thereof |
| US4766106A (en) * | 1985-06-26 | 1988-08-23 | Cetus Corporation | Solubilization of proteins for pharmaceutical compositions using polymer conjugation |
| US4959305A (en) * | 1986-06-18 | 1990-09-25 | Miles Inc. | Reversible immobilization of assay reagents in a multizone test device |
| ES2058121T3 (es) * | 1986-09-17 | 1994-11-01 | Beecham Group Plc | Preparacion enzimatica inmovilizada y su uso. |
| US4894226A (en) * | 1986-11-14 | 1990-01-16 | Cetus Corporation | Solubilization of proteins for pharmaceutical compositions using polyproline conjugation |
| US4847325A (en) * | 1988-01-20 | 1989-07-11 | Cetus Corporation | Conjugation of polymer to colony stimulating factor-1 |
| US5565519A (en) * | 1988-11-21 | 1996-10-15 | Collagen Corporation | Clear, chemically modified collagen-synthetic polymer conjugates for ophthalmic applications |
| US5510418A (en) * | 1988-11-21 | 1996-04-23 | Collagen Corporation | Glycosaminoglycan-synthetic polymer conjugates |
| US5162430A (en) * | 1988-11-21 | 1992-11-10 | Collagen Corporation | Collagen-polymer conjugates |
| US5306500A (en) * | 1988-11-21 | 1994-04-26 | Collagen Corporation | Method of augmenting tissue with collagen-polymer conjugates |
| US5166322A (en) * | 1989-04-21 | 1992-11-24 | Genetics Institute | Cysteine added variants of interleukin-3 and chemical modifications thereof |
| WO1993020838A1 (en) * | 1992-04-20 | 1993-10-28 | Rufeld, Inc. | Method and compositions for treatment of pyonecrotic processes |
| US5545553A (en) * | 1994-09-26 | 1996-08-13 | The Rockefeller University | Glycosyltransferases for biosynthesis of oligosaccharides, and genes encoding them |
| WO1997022371A1 (en) | 1995-12-18 | 1997-06-26 | Collagen Corporation | Crosslinked polymer compositions and methods for their use |
| US6458889B1 (en) | 1995-12-18 | 2002-10-01 | Cohesion Technologies, Inc. | Compositions and systems for forming crosslinked biomaterials and associated methods of preparation and use |
| US6833408B2 (en) * | 1995-12-18 | 2004-12-21 | Cohesion Technologies, Inc. | Methods for tissue repair using adhesive materials |
| US7883693B2 (en) * | 1995-12-18 | 2011-02-08 | Angiodevice International Gmbh | Compositions and systems for forming crosslinked biomaterials and methods of preparation of use |
| EP0874893A2 (en) * | 1995-12-29 | 1998-11-04 | The Procter & Gamble Company | Detergent compositions comprising immobilized enzymes |
| WO1998021302A1 (en) * | 1996-11-14 | 1998-05-22 | Polymer Technology Corporation | Use of water soluble enzyme-polymer conjugates for cleaning contact lenses |
| DK1656952T3 (da) * | 1998-10-16 | 2014-01-20 | Biogen Idec Inc | Polyalkylenglycolkonjugater af interferon beta-1A og anvendelser deraf |
| US7226903B2 (en) * | 2001-10-10 | 2007-06-05 | Neose Technologies, Inc. | Interferon beta: remodeling and glycoconjugation of interferon beta |
| EP2292273A3 (en) | 2001-10-10 | 2011-11-23 | BioGeneriX AG | Remodeling and glycoconjugation of peptides |
| US7157277B2 (en) * | 2001-11-28 | 2007-01-02 | Neose Technologies, Inc. | Factor VIII remodeling and glycoconjugation of Factor VIII |
| US7214660B2 (en) | 2001-10-10 | 2007-05-08 | Neose Technologies, Inc. | Erythropoietin: remodeling and glycoconjugation of erythropoietin |
| US7265084B2 (en) * | 2001-10-10 | 2007-09-04 | Neose Technologies, Inc. | Glycopegylation methods and proteins/peptides produced by the methods |
| US7439043B2 (en) * | 2001-10-10 | 2008-10-21 | Neose Technologies, Inc. | Galactosyl nucleotide sugars |
| US7696163B2 (en) | 2001-10-10 | 2010-04-13 | Novo Nordisk A/S | Erythropoietin: remodeling and glycoconjugation of erythropoietin |
| US7265085B2 (en) * | 2001-10-10 | 2007-09-04 | Neose Technologies, Inc. | Glycoconjugation methods and proteins/peptides produced by the methods |
| US7125843B2 (en) * | 2001-10-19 | 2006-10-24 | Neose Technologies, Inc. | Glycoconjugates including more than one peptide |
| US7173003B2 (en) | 2001-10-10 | 2007-02-06 | Neose Technologies, Inc. | Granulocyte colony stimulating factor: remodeling and glycoconjugation of G-CSF |
| US7297511B2 (en) * | 2001-10-10 | 2007-11-20 | Neose Technologies, Inc. | Interferon alpha: remodeling and glycoconjugation of interferon alpha |
| US8008252B2 (en) * | 2001-10-10 | 2011-08-30 | Novo Nordisk A/S | Factor VII: remodeling and glycoconjugation of Factor VII |
| US7795210B2 (en) * | 2001-10-10 | 2010-09-14 | Novo Nordisk A/S | Protein remodeling methods and proteins/peptides produced by the methods |
| US7179617B2 (en) | 2001-10-10 | 2007-02-20 | Neose Technologies, Inc. | Factor IX: remolding and glycoconjugation of Factor IX |
| US7399613B2 (en) * | 2001-10-10 | 2008-07-15 | Neose Technologies, Inc. | Sialic acid nucleotide sugars |
| US7473680B2 (en) * | 2001-11-28 | 2009-01-06 | Neose Technologies, Inc. | Remodeling and glycoconjugation of peptides |
| DE60336555D1 (de) * | 2002-06-21 | 2011-05-12 | Novo Nordisk Healthcare Ag | Pegylierte glykoformen von faktor vii |
| US8129330B2 (en) * | 2002-09-30 | 2012-03-06 | Mountain View Pharmaceuticals, Inc. | Polymer conjugates with decreased antigenicity, methods of preparation and uses thereof |
| AU2003303513A1 (en) * | 2002-12-30 | 2004-07-29 | Angiotech International Ag | Tissue reactive compounds and compositions and uses thereof |
| WO2004060346A2 (en) | 2002-12-30 | 2004-07-22 | Angiotech International Ag | Drug delivery from rapid gelling polymer composition |
| AU2004221824B2 (en) * | 2003-03-14 | 2009-08-27 | Ratiopharm Gmbh | Branched water-soluble polymers and their conjugates |
| WO2004091499A2 (en) * | 2003-04-09 | 2004-10-28 | Neose Technologies, Inc. | Intracellular formation of peptide conjugates |
| CA2522345A1 (en) * | 2003-04-09 | 2004-11-18 | Neose Technologies, Inc. | Glycopegylation methods and proteins/peptides produced by the methods |
| US8791070B2 (en) | 2003-04-09 | 2014-07-29 | Novo Nordisk A/S | Glycopegylated factor IX |
| US7932364B2 (en) | 2003-05-09 | 2011-04-26 | Novo Nordisk A/S | Compositions and methods for the preparation of human growth hormone glycosylation mutants |
| WO2005012484A2 (en) | 2003-07-25 | 2005-02-10 | Neose Technologies, Inc. | Antibody-toxin conjugates |
| US20080305992A1 (en) * | 2003-11-24 | 2008-12-11 | Neose Technologies, Inc. | Glycopegylated erythropoietin |
| NZ547168A (en) * | 2003-11-24 | 2010-05-28 | Biogenerix Ag | Glycopegylated erythropoietin |
| US8633157B2 (en) * | 2003-11-24 | 2014-01-21 | Novo Nordisk A/S | Glycopegylated erythropoietin |
| ES2422187T3 (es) * | 2003-12-03 | 2013-09-09 | Biogenerix Ag | Factor estimulante de colonias de granulocitos glicopegilados |
| US20060040856A1 (en) * | 2003-12-03 | 2006-02-23 | Neose Technologies, Inc. | Glycopegylated factor IX |
| US7956032B2 (en) * | 2003-12-03 | 2011-06-07 | Novo Nordisk A/S | Glycopegylated granulocyte colony stimulating factor |
| US20080318850A1 (en) * | 2003-12-03 | 2008-12-25 | Neose Technologies, Inc. | Glycopegylated Factor Ix |
| NZ548123A (en) | 2004-01-08 | 2010-05-28 | Novo Nordisk As | O-linked glycosylation of peptides |
| JP4124361B2 (ja) * | 2004-02-16 | 2008-07-23 | 農工大ティー・エル・オー株式会社 | 化学物質の分離方法 |
| NZ550964A (en) | 2004-04-28 | 2011-05-27 | Angiodevice Internat Gmbh | Compositions and systems for forming crosslinked biomaterials and associated methods of preparation and use |
| CA2565414A1 (en) * | 2004-05-04 | 2005-11-24 | Novo Nordisk Health Care Ag | O-linked glycoforms of polypeptides and method to manufacture them |
| WO2006010143A2 (en) | 2004-07-13 | 2006-01-26 | Neose Technologies, Inc. | Branched peg remodeling and glycosylation of glucagon-like peptide-1 [glp-1] |
| WO2006031811A2 (en) * | 2004-09-10 | 2006-03-23 | Neose Technologies, Inc. | Glycopegylated interferon alpha |
| WO2006034128A2 (en) | 2004-09-17 | 2006-03-30 | Angiotech Biomaterials Corporation | Multifunctional compounds for forming crosslinked biomaterials and methods of preparation and use |
| EP1797192A1 (en) * | 2004-09-29 | 2007-06-20 | Novo Nordisk Health Care AG | Modified proteins |
| EP1814573B1 (en) | 2004-10-29 | 2016-03-09 | ratiopharm GmbH | Remodeling and glycopegylation of fibroblast growth factor (fgf) |
| EP1838332A1 (en) * | 2005-01-06 | 2007-10-03 | Neose Technologies, Inc. | Glycoconjugation using saccharyl fragments |
| CA2593682C (en) | 2005-01-10 | 2016-03-22 | Neose Technologies, Inc. | Glycopegylated granulocyte colony stimulating factor |
| US20060246544A1 (en) * | 2005-03-30 | 2006-11-02 | Neose Technologies,Inc. | Manufacturing process for the production of peptides grown in insect cell lines |
| US9187546B2 (en) * | 2005-04-08 | 2015-11-17 | Novo Nordisk A/S | Compositions and methods for the preparation of protease resistant human growth hormone glycosylation mutants |
| WO2006127910A2 (en) * | 2005-05-25 | 2006-11-30 | Neose Technologies, Inc. | Glycopegylated erythropoietin formulations |
| US20080255026A1 (en) * | 2005-05-25 | 2008-10-16 | Glycopegylated Factor 1X | Glycopegylated Factor Ix |
| US20070105755A1 (en) * | 2005-10-26 | 2007-05-10 | Neose Technologies, Inc. | One pot desialylation and glycopegylation of therapeutic peptides |
| MX2008002395A (es) * | 2005-08-19 | 2008-03-18 | Neose Technologies Inc | Factor vii y factor viia glicopegilados. |
| US20090048440A1 (en) | 2005-11-03 | 2009-02-19 | Neose Technologies, Inc. | Nucleotide Sugar Purification Using Membranes |
| CN101516388B (zh) * | 2006-07-21 | 2012-10-31 | 诺和诺德公司 | 通过o-联糖基化序列的肽的糖基化 |
| US8969532B2 (en) * | 2006-10-03 | 2015-03-03 | Novo Nordisk A/S | Methods for the purification of polypeptide conjugates comprising polyalkylene oxide using hydrophobic interaction chromatography |
| WO2008060780A2 (en) * | 2006-10-04 | 2008-05-22 | Novo Nordisk A/S | Glycerol linked pegylated sugars and glycopeptides |
| WO2008073620A2 (en) * | 2006-11-02 | 2008-06-19 | Neose Technologies, Inc. | Manufacturing process for the production of polypeptides expressed in insect cell-lines |
| EP2144923B1 (en) | 2007-04-03 | 2013-02-13 | BioGeneriX AG | Methods of treatment using glycopegylated g-csf |
| US20090053167A1 (en) * | 2007-05-14 | 2009-02-26 | Neose Technologies, Inc. | C-, S- and N-glycosylation of peptides |
| EP2162535A4 (en) * | 2007-06-04 | 2011-02-23 | Novo Nordisk As | O-linked glycosylation using N-acetylglucosamine transferases |
| WO2008154639A2 (en) * | 2007-06-12 | 2008-12-18 | Neose Technologies, Inc. | Improved process for the production of nucleotide sugars |
| US8546328B2 (en) | 2007-08-27 | 2013-10-01 | Biogenerix Ag | Liquid formulation of G-CSF conjugate |
| US8207112B2 (en) * | 2007-08-29 | 2012-06-26 | Biogenerix Ag | Liquid formulation of G-CSF conjugate |
| KR102069498B1 (ko) * | 2007-09-28 | 2020-01-23 | 포톨라 파마슈티컬스, 인코포레이티드 | 인자 Ｘａ 저해제에 대한 안티도트 및 그것을 사용하는 방법 |
| WO2009094172A2 (en) | 2008-01-22 | 2009-07-30 | Araim Pharmaceuticals, Inc. | Tissue protective peptides and peptide analogs for preventing and treating diseases and disorders associated with tissue damage |
| US20130189239A1 (en) | 2008-02-27 | 2013-07-25 | Novo Nordisk A/S | Conjugated Factor VIII Molecules |
| EP2672260A1 (en) | 2008-05-13 | 2013-12-11 | Advanced Liquid Logic, Inc. | Droplet actuator devices, systems and methods |
| HK1200695A1 (en) | 2012-04-16 | 2015-08-14 | Cantab Biopharmaceuticals Patents Limited | Optimised subcutaneous therapeutic agents |
| JP2019523633A (ja) | 2016-04-29 | 2019-08-29 | アライム ファーマシューティカルズ，インコーポレーテッド | 組織の損傷に関連した疾患及び障害を予防及び治療する組織保護ペプチド |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6812443A (enExample) * | 1968-08-31 | 1970-03-03 | ||
| US3625827A (en) * | 1968-09-27 | 1971-12-07 | Monsanto Co | Water-soluble polymer-enzyme products |
| US3649457A (en) * | 1968-09-27 | 1972-03-14 | Monsanto Co | Enzymatic processing with polymer-enzyme product |
| US3576760A (en) * | 1969-06-13 | 1971-04-27 | Nat Patent Dev Corp | Water soluble entrapping |
| GB1353317A (en) * | 1970-03-03 | 1974-05-15 | Koninklijke Gist Spiritus | Enzyme-polymer complexes |
| US3695999A (en) * | 1970-07-22 | 1972-10-03 | Peter Salvatore Forgione | Isolation of enzymes from aqueous media by means of polyanions |
| CH581664A5 (enExample) * | 1974-02-21 | 1976-11-15 | Nestle Sa | |
| US4017364A (en) * | 1975-06-19 | 1977-04-12 | Societe D'assistance Technique Pour Produits Nestle S.A. | Process for producing an enzyme product having variable solubility |
-
1975
- 1975-05-30 CH CH696575A patent/CH596313A5/xx not_active IP Right Cessation
-
1976
- 1976-05-26 GB GB21811/76A patent/GB1554211A/en not_active Expired
- 1976-05-26 DE DE2624002A patent/DE2624002C2/de not_active Expired
- 1976-05-26 US US05/690,096 patent/US4088538A/en not_active Expired - Lifetime
- 1976-05-26 FR FR7616023A patent/FR2312561A1/fr active Granted
- 1976-05-28 JP JP51061294A patent/JPS5840474B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH596313A5 (enExample) | 1978-03-15 |
| FR2312561A1 (fr) | 1976-12-24 |
| DE2624002C2 (de) | 1984-06-20 |
| GB1554211A (en) | 1979-10-17 |
| DE2624002A1 (de) | 1976-12-09 |
| US4088538A (en) | 1978-05-09 |
| FR2312561B1 (enExample) | 1980-06-06 |
| JPS51144787A (en) | 1976-12-13 |
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