DE2613011A1 - Verfahren zur herstellung traegergebundener biologisch aktiver verbindungen - Google Patents
Verfahren zur herstellung traegergebundener biologisch aktiver verbindungenInfo
- Publication number
- DE2613011A1 DE2613011A1 DE19762613011 DE2613011A DE2613011A1 DE 2613011 A1 DE2613011 A1 DE 2613011A1 DE 19762613011 DE19762613011 DE 19762613011 DE 2613011 A DE2613011 A DE 2613011A DE 2613011 A1 DE2613011 A1 DE 2613011A1
- Authority
- DE
- Germany
- Prior art keywords
- biologically active
- carrier
- ions
- oxidation
- bound
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 6
- 229920000642 polymer Polymers 0.000 claims description 12
- 238000007254 oxidation reaction Methods 0.000 claims description 11
- 150000002500 ions Chemical class 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 8
- 239000013543 active substance Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 108090000790 Enzymes Proteins 0.000 claims description 4
- 102000004190 Enzymes Human genes 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- -1 alkali metal arsenates Chemical class 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000000427 antigen Substances 0.000 claims description 2
- 102000036639 antigens Human genes 0.000 claims description 2
- 108091007433 antigens Proteins 0.000 claims description 2
- 239000005515 coenzyme Substances 0.000 claims description 2
- 239000002532 enzyme inhibitor Substances 0.000 claims description 2
- 239000005556 hormone Substances 0.000 claims description 2
- 229940088597 hormone Drugs 0.000 claims description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical group NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 229910021538 borax Inorganic materials 0.000 description 7
- 239000004328 sodium tetraborate Substances 0.000 description 7
- 235000010339 sodium tetraborate Nutrition 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 108090000631 Trypsin Proteins 0.000 description 6
- 102000004142 Trypsin Human genes 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000012588 trypsin Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 108010015776 Glucose oxidase Proteins 0.000 description 5
- 239000004366 Glucose oxidase Substances 0.000 description 5
- 229940116332 glucose oxidase Drugs 0.000 description 5
- 235000019420 glucose oxidase Nutrition 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 108090000317 Chymotrypsin Proteins 0.000 description 3
- 108010038061 Chymotrypsinogen Proteins 0.000 description 3
- 125000003277 amino group Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229960002376 chymotrypsin Drugs 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 229940088598 enzyme Drugs 0.000 description 3
- YAGKRVSRTSUGEY-UHFFFAOYSA-N ferricyanide Chemical compound [Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] YAGKRVSRTSUGEY-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000008351 acetate buffer Substances 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 238000001042 affinity chromatography Methods 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000223290 Hypherpes complex Species 0.000 description 1
- 102000057297 Pepsin A Human genes 0.000 description 1
- 108090000284 Pepsin A Proteins 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229940000488 arsenic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- ZURAKLKIKYCUJU-UHFFFAOYSA-N copper;azane Chemical compound N.[Cu+2] ZURAKLKIKYCUJU-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229960000789 guanidine hydrochloride Drugs 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229940111202 pepsin Drugs 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 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
- C12N11/08—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
-
- 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
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/815—Test for named compound or class of compounds
- Y10S436/817—Steroids or hormones
Landscapes
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS7500002132A CS181417B1 (en) | 1975-03-27 | 1975-03-27 | Method for preparing insoluble biologically active compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2613011A1 true DE2613011A1 (de) | 1976-10-07 |
Family
ID=5357554
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762613011 Withdrawn DE2613011A1 (de) | 1975-03-27 | 1976-03-26 | Verfahren zur herstellung traegergebundener biologisch aktiver verbindungen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4085005A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS5946596B2 (cg-RX-API-DMAC10.html) |
| CA (1) | CA1054081A (cg-RX-API-DMAC10.html) |
| CS (1) | CS181417B1 (cg-RX-API-DMAC10.html) |
| DE (1) | DE2613011A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2305441A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1499357A (cg-RX-API-DMAC10.html) |
| SE (1) | SE430069B (cg-RX-API-DMAC10.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4180629A (en) * | 1974-10-30 | 1979-12-25 | Ceskoslovenska Akademie Ved | Polymers containing a reactive aromatic system based on p-phenylenediamine derivatives |
| US4530963A (en) * | 1982-08-20 | 1985-07-23 | Devoe-Holbein International, N.V. | Insoluble chelating compositions |
| GB8334499D0 (en) * | 1983-12-24 | 1984-02-01 | Beecham Group Plc | Derivatives |
| US4952519A (en) * | 1988-05-02 | 1990-08-28 | E. I. Du Pont De Nemours And Company | Protein immobilization with poly(ethyleneimine) derivatized with a hydroprobic group |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3706633A (en) * | 1970-04-10 | 1972-12-19 | Monsanto Co | Preparation of water-insoluble enzyme derivatives |
| US3745088A (en) * | 1970-12-23 | 1973-07-10 | Us Agriculture | Active water-insoluble enzymes |
| US3970521A (en) * | 1974-08-07 | 1976-07-20 | Exxon Research And Engineering Company | Immobilized glycoenzymes |
-
1975
- 1975-03-27 CS CS7500002132A patent/CS181417B1/cs unknown
-
1976
- 1976-03-24 US US05/669,866 patent/US4085005A/en not_active Expired - Lifetime
- 1976-03-25 GB GB12042/76A patent/GB1499357A/en not_active Expired
- 1976-03-25 SE SE7603640A patent/SE430069B/xx not_active IP Right Cessation
- 1976-03-26 JP JP51032673A patent/JPS5946596B2/ja not_active Expired
- 1976-03-26 DE DE19762613011 patent/DE2613011A1/de not_active Withdrawn
- 1976-03-26 FR FR7608802A patent/FR2305441A1/fr active Granted
- 1976-03-26 CA CA249,108A patent/CA1054081A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1499357A (en) | 1978-02-01 |
| CS181417B1 (en) | 1978-03-31 |
| CA1054081A (en) | 1979-05-08 |
| SE430069B (sv) | 1983-10-17 |
| JPS5946596B2 (ja) | 1984-11-13 |
| FR2305441B1 (cg-RX-API-DMAC10.html) | 1980-03-28 |
| US4085005A (en) | 1978-04-18 |
| SE7603640L (sv) | 1976-09-28 |
| FR2305441A1 (fr) | 1976-10-22 |
| JPS51117784A (en) | 1976-10-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8110 | Request for examination paragraph 44 | ||
| 8139 | Disposal/non-payment of the annual fee |