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
Authority: JP; Japan
Prior art keywords: enzyme; complex; enzyme complex; reaction; substance
Prior art date: 1975-05-30
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

Application number

JP51061294A

Other languages

English (en)

Japanese (ja)

Other versions

JPS51144787A (en

Inventor

ミツシエル・シユナイダー

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Battelle Memorial Institute Inc

Original Assignee

Battelle Memorial Institute Inc

Priority date (The priority date 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 date listed.)

1975-05-30

Filing date

1976-05-28

Publication date

1983-09-06

1976-05-28 Application filed by Battelle Memorial Institute Inc filed Critical Battelle Memorial Institute Inc

1976-12-13 Publication of JPS51144787A publication Critical patent/JPS51144787A/ja

1983-09-06 Publication of JPS5840474B2 publication Critical patent/JPS5840474B2/ja

Status Expired legal-status Critical Current

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)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Molecular Biology (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Emergency Medicine (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Immobilizing And Processing Of Enzymes And Microorganisms (AREA)

JP51061294A 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 Expired JPS5840474B2 (ja)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH696575A CH596313A5 (2)	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 (2)
JP (1)	JPS5840474B2 (2)
CH (1)	CH596313A5 (2)
DE (1)	DE2624002C2 (2)
FR (1)	FR2312561A1 (2)
GB (1)	GB1554211A (2)

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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
DE3786511T2 (de) *	1986-09-17	1994-01-13	Beecham Group Plc	Immobilisiertes Enzympräparat und seine Verwendung.
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
US5510418A (en) *	1988-11-21	1996-04-23	Collagen Corporation	Glycosaminoglycan-synthetic polymer conjugates
US5306500A (en) *	1988-11-21	1994-04-26	Collagen Corporation	Method of augmenting tissue with collagen-polymer conjugates
US5565519A (en) *	1988-11-21	1996-10-15	Collagen Corporation	Clear, chemically modified collagen-synthetic polymer conjugates for ophthalmic applications
US5162430A (en) *	1988-11-21	1992-11-10	Collagen Corporation	Collagen-polymer conjugates
US5166322A (en) *	1989-04-21	1992-11-24	Genetics Institute	Cysteine added variants of interleukin-3 and chemical modifications thereof
AU4104093A (en) *	1992-04-20	1993-11-18	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
ATE330644T1 (de) *	1995-12-18	2006-07-15	Angiotech Biomaterials Corp	Vernetzten polymerisatmassen und verfahren für ihre verwendung
US6833408B2 (en) *	1995-12-18	2004-12-21	Cohesion Technologies, Inc.	Methods for tissue repair using adhesive materials
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
US7883693B2 (en)	1995-12-18	2011-02-08	Angiodevice International Gmbh	Compositions and systems for forming crosslinked biomaterials and methods of preparation of use
US6030933A (en) *	1995-12-29	2000-02-29	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
US7157277B2 (en) *	2001-11-28	2007-01-02	Neose Technologies, Inc.	Factor VIII remodeling and glycoconjugation of Factor VIII
US7399613B2 (en) *	2001-10-10	2008-07-15	Neose Technologies, Inc.	Sialic acid nucleotide sugars
US7179617B2 (en)	2001-10-10	2007-02-20	Neose Technologies, Inc.	Factor IX: remolding and glycoconjugation of Factor IX
US7173003B2 (en)	2001-10-10	2007-02-06	Neose Technologies, Inc.	Granulocyte colony stimulating factor: remodeling and glycoconjugation of G-CSF
US7265085B2 (en) *	2001-10-10	2007-09-04	Neose Technologies, Inc.	Glycoconjugation methods and proteins/peptides produced by the methods
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- 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 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
DE2624002A1 (de)	1976-12-09
JPS51144787A (en)	1976-12-13
FR2312561A1 (fr)	1976-12-24
US4088538A (en)	1978-05-09
DE2624002C2 (de)	1984-06-20
CH596313A5 (2)	1978-03-15
FR2312561B1 (2)	1980-06-06
GB1554211A (en)	1979-10-17

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