DE2036499A1 - Stable,insoluble enzyme prepns - with enzyme linked to glass carrier by organosilane - Google Patents
Stable,insoluble enzyme prepns - with enzyme linked to glass carrier by organosilaneInfo
- Publication number
- DE2036499A1 DE2036499A1 DE19702036499 DE2036499A DE2036499A1 DE 2036499 A1 DE2036499 A1 DE 2036499A1 DE 19702036499 DE19702036499 DE 19702036499 DE 2036499 A DE2036499 A DE 2036499A DE 2036499 A1 DE2036499 A1 DE 2036499A1
- Authority
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- Germany
- Prior art keywords
- enzyme
- bound
- coupling agent
- silane
- insoluble
- 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.)
- Pending
Links
- 102000004190 Enzymes Human genes 0.000 title claims abstract description 47
- 108090000790 Enzymes Proteins 0.000 title claims abstract description 47
- 239000011521 glass Substances 0.000 title claims abstract description 6
- 150000001282 organosilanes Chemical class 0.000 title 1
- 239000000758 substrate Substances 0.000 claims abstract description 11
- 239000007822 coupling agent Substances 0.000 claims abstract description 9
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 238000009835 boiling Methods 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 238000002360 preparation method Methods 0.000 claims description 5
- 229910000077 silane Inorganic materials 0.000 claims description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 3
- -1 N-beta-aminoethyl- (alpha-methyl-gamma-aminopropyl) Chemical group 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 150000004756 silanes Chemical class 0.000 abstract description 6
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 230000002255 enzymatic effect Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000012412 chemical coupling Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- XYYQWMDBQFSCPB-UHFFFAOYSA-N dimethoxymethylsilane Chemical compound COC([SiH3])OC XYYQWMDBQFSCPB-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- VWWQXMAJTJZDQX-UYBVJOGSSA-N flavin adenine dinucleotide Chemical group C1=NC2=C(N)N=CN=C2N1[C@@H]([C@H](O)[C@@H]1O)O[C@@H]1CO[P@](O)(=O)O[P@@](O)(=O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C2=NC(=O)NC(=O)C2=NC2=C1C=C(C)C(C)=C2 VWWQXMAJTJZDQX-UYBVJOGSSA-N 0.000 description 1
- 235000019162 flavin adenine dinucleotide Nutrition 0.000 description 1
- 239000011714 flavin adenine dinucleotide Substances 0.000 description 1
- 229940093632 flavin-adenine dinucleotide Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical class [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 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
- C12N11/14—Enzymes or microbial cells immobilised on or in an inorganic carrier
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Molecular Biology (AREA)
- Immunology (AREA)
- Biophysics (AREA)
- Inorganic Chemistry (AREA)
- Biomedical Technology (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Enzymes And Modification Thereof (AREA)
Abstract
Description
,8tabilisiertes Enzympräparat und Verfahren zu seiner Herstellung Das Hauptpatent (Patentanmeldung P 19 44 418.9) betrifft die Stabilisierung von Enzymen durch chemische Kuppelung der Enzyme an eine anorganische Trägersubstanz vermittels eines Kupplungsmittels in Form eines Silans, wobei das Enzym unlöslich wird und über einen langeren Zeitraum verwendet und wieder verwendet werden kann., 8 stabilized enzyme preparation and process for its production The main patent (patent application P 19 44 418.9) relates to the stabilization of Enzymes through chemical coupling of the enzymes to an inorganic carrier substance by means of a coupling agent in the form of a silane, the enzyme being insoluble and can be used and reused over a long period of time.
Ein Enzym ist ein biologischer Katalysator, der fähig ist, eine chemische Reaktion in Gang zu setzen, zu fördern und zu leiten, ohne dass es beim Prozess aufgebraucht oder zu einem Teil des gebildeten Produkts wird. Enzyme werden z.An enzyme is a biological catalyst that is capable of producing a chemical Initiate, encourage, and guide response without affecting the process is used up or becomes part of the product formed. Enzymes are z.
B. durch Pflanzen, Tiere und Mikroorganismen synthetisiert.B. synthesized by plants, animals and microorganisms.
Alle bisher isolierten Enzyme sind Proteine, d. h. Peptidpolymere von Aminosäuren. Ein Enzym kann prosthetische Gruppen wie Flavin-adenin-dinucleotid, Porphyrin, Diphosphopyridin-nucleotid usw. enthalten. Enzyme sind im allgemeinen Makromoleküle, mit einem Molekulargewicht über 6000.All enzymes isolated so far are proteins; H. Peptide polymers of amino acids. An enzyme can have prosthetic groups such as flavin adenine dinucleotide, Contain porphyrin, diphosphopyridine nucleotide, etc. Enzymes are in general Macromolecules, with a molecular weight over 6000.
Der isoelektrische Punkt der Enzyme liegt bei einem pH-Wert von etwas weniger als 1,0 bis 11,0. Bei oder. in der Nahe dieser Wasserstoffionenkonzentration neigen die EnzFm-Proteine gewöhnlich zum Koagulieren.The isoelectric point of the enzymes is around a pH of something less than 1.0 to 11.0. With or. near this hydrogen ion concentration the EnzFm proteins usually tend to coagulate.
Die besonderen Eigenschaften der Enzyme und ihre Fähigkeit, Reaktionen von Substraten bei niedrigen Konzentrationen zu katalysieren, ist in der chemischen Analyse von besonderem Interesse. Durch Enzyme katalysierte Reaktionen sind seit einiger Zeit zur qualitativen und quantitativen Bestimmung von Substraten, Beschleunigern,-Verzögerern, und auch von Enzymen selbst verwendet worden. Bis in die åüngste Zeit haben die bei Verwendung von Enzymen auftretenden Nachteile ihre Brauchbarkeit stark eingeschränkt. Einwände gegen die Verwendung von Enzymen sind ihre Unstabilität, ihr Mangel an Verfügbarkeit, geringe Genauigkeit, sowie der Arbeitsaufwand zur Durchführung der Analyse. Weiterhin sind die Kosten bei Verwendung grosser Enzymmengen in der analytischen Chemie, besonders bei Routineanalysen, ein besonders schwieriges Problem. Da die bekannten Enzyme Proteine sind, werden sie wie diese unter bestimmten Bedingungen, z. B. Temperaturen, pH-Werten, Konzentrationen, Mikrobenbefall, Autohydrolyse und derglichen denaturiert.The special properties of enzymes and their ability to react Catalyzing substrates at low concentrations is in chemical Analysis of particular interest. Reactions catalyzed by enzymes have been around since some time for the qualitative and quantitative determination of substrates, accelerators, retarders, and has also been used by enzymes themselves. Until recently they have disadvantages occurring when using enzymes their usefulness highly limited. Objections to the use of enzymes are their instability, their lack of availability, poor accuracy, as well as the amount of work required to carry them out the analysis. Furthermore, the costs when using large amounts of enzyme are in the analytical chemistry, especially in routine analysis, is a particularly difficult problem. Since the known enzymes are proteins, they become like these under certain conditions, z. B. Temperatures, pH values, concentrations, microbe infestation, autohydrolysis and such denatured.
Es sind Versuche unternommen worden, Enzyme in gebundener Form ohne Verlust ihrer Wirksamkeit herzustellen, so dass eine Probe kontinuierlich viele Stunden benutzt werden kann.Attempts have been made to use enzymes in bound form without Loss of their effectiveness to produce so that one sample continuously many Hours can be used.
Das gebundene Enzym wird in der gleichen Weise verwendet wie lösliche Enzyme, d. h. zur Bestimmung der Konzentration eines Substrates, eines Inhibitors, der das Enzym inaktiviert, oder eines Aktivators, der eine Beschleunigung der Enzymaktivität bewirkt, wobei aber die Genauigkeit verbessert ist. Enzyme sind diazotiert an Celluloseteilchen und Polyaminostyrolperlen worden. tuch wurde versucht, die Enzyme durch Adsorption, Absorption oder durch Ionenaustausch physikalisch einzuhüllen. Enzyme sind auch an Polystyrolpolypeptide gebunden, und in Kollodivininatrizen in Starkes oder Polyacrylsmidgelen, Agar, usw. und in semipermeable Zikrokapseln aus sznthetischen Polymerisaten eingeschlossen worden, Alle bisher zum Binden der Enzyme verwendeten Urägersubstanzen waren organische Substanzen, besonders organische Polymerisate. Der Hauptnachteil bei Verwerdung von organischem Material beruht darauf, dass sie gegen Mikrobenbefall infolge der Anwesenneit von C-Atomen in der polymeren Kette anfällig sind, wobei der Träger aufgebrochen und das Enzym löslich gemacht wird. Weiterhin erfolgt die Kupplung mit Hilfe von Diazobindung durch eine Kupplungsgruppe, wobei die Enzymmoleküle an den Träger nur an verschiedenen Punkten entlang der Enzymkette gebunden sind. In wässriger Lösung können die Moleküle auseinanderfallen, wobei das Protein denaturiert und dementsprechend ein Verlust an EnzFmwirksam keit auftritt.The bound enzyme is used in the same way as soluble Enzymes, d. H. to determine the concentration of a substrate, an inhibitor, that inactivates the enzyme, or an activator that accelerates enzyme activity causes, but the accuracy is improved. Enzymes are diazotized on cellulose particles and polyaminostyrene beads. an attempt was made to remove the enzymes by adsorption, Physically encapsulated by absorption or by ion exchange. Enzymes are too bound to polystyrene polypeptides, and in Kollodivin matrices in Strong or polyacrylic midgels, agar, etc. and made in semipermeable microcapsules Synthetic polymers have been included, all so far for binding the enzymes The original substances used were organic substances, especially organic polymers. The main disadvantage of disposing of organic material is that it against microbial infestation due to the presence of carbon atoms in the polymer chain are susceptible, breaking the support and solubilizing the enzyme. Furthermore, the coupling takes place with the aid of a diazo bond through a coupling group, whereby the enzyme molecules attach to the carrier only at different points along the enzyme chain are bound. In aqueous solution the molecules can fall apart, whereby the protein denatures and a corresponding loss of enzyme efficiency occurs.
In vielen Fällen wird die Substratdiffusion zum Grenzwert der Umsetzungsgeschwindigkeit und vermindert die scheinbare Enzymaktivität. Bei Verwendung in chromatogtaphischen Säulen bewirken die pH-Werte und Lösungsverhältnisse eine Zu-oder abnahme der Anschwellung, die den Substratdurchsatz in der Säule unkontrolliert und unerwunscht beeinflussen.In many cases the substrate diffusion becomes the limit value of the conversion rate and reduces the apparent enzyme activity. When used in chromatographic Columns cause the pH values and solution ratios to increase or decrease the swelling, which influence the substrate throughput in the column in an uncontrolled and undesired way.
In dem Patent der früheren Anmeldung P 19 05 681.6-41 ist bereits ein im wesentlichen wasserunlösliches, stabilisiertes Enzympräparat und ein Verfahren zu seiner Herstellung beschrieben, in dem das freie Aminogruppen aufweisende Enzym an einen anorganischen, eine grosse Oberfläche und reaktive Silanolgruppen aufweisenden Träger durch Amino-Silikat- und Wasserstoffbindung gekuppelt ist. Die Kupplung des Enzyms an den Träger ist eine unmittelbare. Dies hat den Nachteil, dass bei eventueller Bindung an die aktiven Stellen des.In the patent of the earlier application P 19 05 681.6-41 is already a substantially water-insoluble, stabilized enzyme preparation and method described for its preparation, in which the enzyme containing free amino groups an inorganic one that has a large surface area and reactive silanol groups Carrier is coupled by amino-silicate and hydrogen bonding. The coupling of the Enzyme to the carrier is immediate. This has the disadvantage that with eventual Binding to the active sites of the.
Enzymmoleküls die Aktivität gegebenenfalls beeinträchtigt werden kann.Enzyme molecule the activity can possibly be impaired.
.terraschenderweise wurde nach dem Hauptpatent (Patentanmeidung P 19 44 418.9) gefunden, dass dieser Nachteil durch Zwischenschaltung eines geeigneten Kupplungsmittels in Form eines Silans überwunden werden kann. Dabei werden die übrigen, gegenüber dem obenbezeichneten Stand der Technik erreichten Vorteile, insbesondere verbesserte langwährende Stabilität, weitgehende Immunität gegen Nikrobenbefall etc.Surprisingly, after the main patent (patent application P 19 44 418.9) found that this disadvantage through the interposition of a suitable Coupling agent in the form of a silane can be overcome. The rest of the advantages achieved over the above-mentioned prior art, in particular improved long-term stability, extensive immunity against microbe infestation Etc.
ebenfalls erzielt.also achieved.
Der erfindungsgemässe Lösungsvorschlag des Hauptpatents geht dahin, dass ein Enzym an einen anorganischen, freie g oxyl- oder Oxidgruppen aufweisenden Träger vermittels eines Silankupplungsmittels kovalent gebunden ist, wobei der Siliziumteil des Silanmoleküls an den Träger und der organische Teil an das Enzym gebunden ist.The proposed solution according to the invention of the main patent goes as follows that an enzyme to an inorganic, free g oxyl or oxide groups Carrier mediating of a silane coupling agent covalently bonded where the silicon part of the silane molecule is attached to the carrier and the organic part bound to the enzyme.
Nach dem Hauptpatent weist nur das Silankupplungsmittel die allgemeine Formel auf: Yn SiR4-n (Y'R')nSiR4-n oder auch die allgemeine ' (Y'R')nSiR4-n .According to the main patent, only the silane coupling agent has the general one Formula based on: Yn SiR4-n (Y'R ') nSiR4-n or the general' (Y'R ') nSiR4-n.
Die vorliegende Anmeldung hat nun besonders günstige Eupplungsmittel sowie deren besonders wirksame Aufbringung auf das Glassubstrat zur Aufgabe und schlägt als Lösung das folgende vor: Nach einer Ausführungsform der Erfindung sind die Kupplungsmittel Amino-funktionelle Silane wie z. B. N-beta-Aminoäthylgamma-Äminopropyltrimethoxylan, N-beta-Aminoäthyl-(alpha-Methyl-gamma-Aminopropy Dimethoxymethylsilan oder gamma-Aminopropyl-Triäthosilan. Das Kupplungsmittel wird auf das Glassubstrat aus einer Lösung aufgebracht. Als Lösungsmittel eignen sich hierfür nur die höher siedenden aromatischen und aliphatischen Löser. Besonders geeignet sind Toluol, Benzol, Xylol und hochsiedende Kohlenwasserstoffe.The present application now has particularly inexpensive coupling agents and their particularly effective application to the glass substrate for the task and proposes the following as a solution: According to one embodiment of the invention, are the coupling agent amino-functional silanes such. B. N-beta-Aminoäthylgamma-Äminopropyltrimethoxylan, N-beta-aminoethyl- (alpha-methyl-gamma-aminopropy dimethoxymethylsilane or gamma-aminopropyl-triethosilane. The coupling agent is applied to the glass substrate from a solution. as Only the higher-boiling aromatic and aliphatic solvents are suitable for this Solver. Are particularly suitable Toluene, benzene, xylene and high boiling points Hydrocarbons.
Obwohl die Silane auch in Alkohol und Wasser löslich sind, sollten diese vermleden werden, da sie eine gute Bindung beeinträchtigen. Vermieden werden sollten auch die Aldehyde, Ketone, Säuren, Ester oder Alkylchloride, da sie zur Umsetzung mit den Silanen neigen. Although the silanes are also soluble in alcohol and water, they should these are avoided as they impair a good bond. Be avoided should also include the aldehydes, ketones, acids, esters or alkyl chlorides as they are used to Tend to implement with the silanes.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702036499 DE2036499A1 (en) | 1970-07-23 | 1970-07-23 | Stable,insoluble enzyme prepns - with enzyme linked to glass carrier by organosilane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702036499 DE2036499A1 (en) | 1970-07-23 | 1970-07-23 | Stable,insoluble enzyme prepns - with enzyme linked to glass carrier by organosilane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2036499A1 true DE2036499A1 (en) | 1972-02-03 |
Family
ID=5777595
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702036499 Pending DE2036499A1 (en) | 1970-07-23 | 1970-07-23 | Stable,insoluble enzyme prepns - with enzyme linked to glass carrier by organosilane |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2036499A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4886740A (en) * | 1985-06-05 | 1989-12-12 | Imperial Chemical Industries Plc | Enzyme-electrode sensor with organosilane treated membrane |
| EP0530496A1 (en) * | 1991-07-30 | 1993-03-10 | Dow Corning Toray Silicone Company, Limited | Organosilicon compounds and method for preparing same |
-
1970
- 1970-07-23 DE DE19702036499 patent/DE2036499A1/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4886740A (en) * | 1985-06-05 | 1989-12-12 | Imperial Chemical Industries Plc | Enzyme-electrode sensor with organosilane treated membrane |
| EP0530496A1 (en) * | 1991-07-30 | 1993-03-10 | Dow Corning Toray Silicone Company, Limited | Organosilicon compounds and method for preparing same |
| US5272243A (en) * | 1991-07-30 | 1993-12-21 | Dow Corning Toray Silicone Co., Ltd. | Organosilicon compounds and method for preparing same |
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