CA1087608A - Method for immobilizing protein on a carrier - Google Patents
Method for immobilizing protein on a carrierInfo
- Publication number
- CA1087608A CA1087608A CA267,721A CA267721A CA1087608A CA 1087608 A CA1087608 A CA 1087608A CA 267721 A CA267721 A CA 267721A CA 1087608 A CA1087608 A CA 1087608A
- Authority
- CA
- Canada
- Prior art keywords
- protein
- groups
- reacted
- process according
- group
- 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
- 102000004169 proteins and genes Human genes 0.000 title claims abstract description 85
- 108090000623 proteins and genes Proteins 0.000 title claims abstract description 85
- 238000000034 method Methods 0.000 title claims abstract description 31
- 230000003100 immobilizing effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 23
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 21
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 20
- JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical group ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 16
- 239000000047 product Substances 0.000 claims abstract description 15
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 239000003125 aqueous solvent Substances 0.000 claims abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 230000008569 process Effects 0.000 claims description 24
- -1 sulphhydryl groups Chemical group 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 20
- 239000004952 Polyamide Substances 0.000 claims description 14
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 14
- 229920002647 polyamide Polymers 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 9
- 239000012876 carrier material Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 5
- 125000004185 ester group Chemical group 0.000 claims description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 5
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- MPTQLFFTNNKMRP-UHFFFAOYSA-N 3,4-dihydroxypyrrolidine-2,5-dione Chemical class OC1C(O)C(=O)NC1=O MPTQLFFTNNKMRP-UHFFFAOYSA-N 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001302 tertiary amino group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000005442 diisocyanate group Chemical group 0.000 claims description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
- ZETHHMPKDUSZQQ-UHFFFAOYSA-N Betulafolienepentol Natural products C1C=C(C)CCC(C(C)CCC=C(C)C)C2C(OC)OC(OC)C2=C1 ZETHHMPKDUSZQQ-UHFFFAOYSA-N 0.000 claims 1
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004036 acetal group Chemical group 0.000 claims 1
- 150000001336 alkenes Chemical group 0.000 claims 1
- HEOKFDGOFROELJ-UHFFFAOYSA-N diacetal Natural products COc1ccc(C=C/c2cc(O)cc(OC3OC(COC(=O)c4cc(O)c(O)c(O)c4)C(O)C(O)C3O)c2)cc1O HEOKFDGOFROELJ-UHFFFAOYSA-N 0.000 claims 1
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 1
- 125000002560 nitrile group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 3
- 229940070376 protein Drugs 0.000 abstract 1
- 235000018102 proteins Nutrition 0.000 description 56
- 239000000243 solution Substances 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000008363 phosphate buffer Substances 0.000 description 17
- 230000000694 effects Effects 0.000 description 16
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
- 239000004677 Nylon Substances 0.000 description 15
- 229920001778 nylon Polymers 0.000 description 15
- 108010015776 Glucose oxidase Proteins 0.000 description 14
- 239000004366 Glucose oxidase Substances 0.000 description 14
- 229940116332 glucose oxidase Drugs 0.000 description 14
- 235000019420 glucose oxidase Nutrition 0.000 description 14
- 239000008187 granular material Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 12
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 229920002292 Nylon 6 Polymers 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 8
- 239000000872 buffer Substances 0.000 description 8
- 229950005499 carbon tetrachloride Drugs 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 125000006850 spacer group Chemical group 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 229940088598 enzyme Drugs 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 229960004418 trolamine Drugs 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- HGAZMNJKRQFZKS-UHFFFAOYSA-N chloroethene;ethenyl acetate Chemical compound ClC=C.CC(=O)OC=C HGAZMNJKRQFZKS-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- SWRGUMCEJHQWEE-UHFFFAOYSA-N ethanedihydrazide Chemical compound NNC(=O)C(=O)NN SWRGUMCEJHQWEE-UHFFFAOYSA-N 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 102000015081 Blood Coagulation Factors Human genes 0.000 description 1
- 108010039209 Blood Coagulation Factors Proteins 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 108010050375 Glucose 1-Dehydrogenase Proteins 0.000 description 1
- 102000057621 Glycerol kinases Human genes 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 101710163410 Probable glycerol kinase Proteins 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003114 blood coagulation factor Substances 0.000 description 1
- HCOMFAYPHBFMKU-UHFFFAOYSA-N butanedihydrazide Chemical compound NNC(=O)CCC(=O)NN HCOMFAYPHBFMKU-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000019628 coolness Nutrition 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- RZVGUUMNWCDIBV-UHFFFAOYSA-N diethyl propanediimidate Chemical compound CCOC(=N)CC(=N)OCC RZVGUUMNWCDIBV-UHFFFAOYSA-N 0.000 description 1
- ZLFRJHOBQVVTOJ-UHFFFAOYSA-N dimethyl hexanediimidate Chemical compound COC(=N)CCCCC(=N)OC ZLFRJHOBQVVTOJ-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 150000002463 imidates Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001308 poly(aminoacid) Polymers 0.000 description 1
- 108010011110 polyarginine Proteins 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 210000002268 wool Anatomy 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
- C12N11/089—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
- C12N11/096—Polyesters; Polyamides
-
- 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
- Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
- Y10S530/81—Carrier - bound or immobilized peptides or proteins and the preparation thereof, e.g. biological cell or cell fragment as carrier
- Y10S530/812—Peptides or proteins is immobilized on, or in, an organic carrier
-
- 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
- Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
- Y10S530/81—Carrier - bound or immobilized peptides or proteins and the preparation thereof, e.g. biological cell or cell fragment as carrier
- Y10S530/812—Peptides or proteins is immobilized on, or in, an organic carrier
- Y10S530/815—Carrier is a synthetic polymer
- Y10S530/816—Attached to the carrier via a bridging agent
Landscapes
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Biomedical Technology (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Polyamides (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2603319.2 | 1976-01-29 | ||
| DE2603319A DE2603319C3 (de) | 1976-01-29 | 1976-01-29 | Verfahren zur Fixierung von biologisch aktiven Proteinen an Trägern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1087608A true CA1087608A (en) | 1980-10-14 |
Family
ID=5968538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA267,721A Expired CA1087608A (en) | 1976-01-29 | 1976-12-13 | Method for immobilizing protein on a carrier |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4119589A (OSRAM) |
| JP (1) | JPS5294489A (OSRAM) |
| AT (1) | AT359021B (OSRAM) |
| AU (1) | AU509729B2 (OSRAM) |
| BE (1) | BE850717A (OSRAM) |
| CA (1) | CA1087608A (OSRAM) |
| CH (1) | CH626092A5 (OSRAM) |
| DD (1) | DD128404A5 (OSRAM) |
| DE (1) | DE2603319C3 (OSRAM) |
| DK (1) | DK36377A (OSRAM) |
| FR (1) | FR2339620A1 (OSRAM) |
| GB (1) | GB1521243A (OSRAM) |
| HU (1) | HU176482B (OSRAM) |
| IL (1) | IL51126A (OSRAM) |
| IT (1) | IT1065504B (OSRAM) |
| NL (1) | NL7614014A (OSRAM) |
| SE (1) | SE7700761L (OSRAM) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2528806A (en) * | 1945-11-09 | 1950-11-07 | Deere & Co | Beet harvester |
| DE2708018A1 (de) | 1977-02-24 | 1978-09-07 | Boehringer Mannheim Gmbh | An polyamid fixiertes biologisch aktives protein und verfahren zu seiner herstellung |
| US4415490A (en) * | 1979-07-24 | 1983-11-15 | Nippon Zeon Co., Ltd. | Non-thrombogenic material |
| US4279787A (en) * | 1979-07-30 | 1981-07-21 | Tetra Consultants Inc. | Method of binding antigens to insoluble polymeric substances |
| WO1981001145A1 (en) * | 1979-10-18 | 1981-04-30 | Univ Illinois | Hydrolytic enzyme-activatible pro-drugs |
| JPS5670028A (en) * | 1979-11-12 | 1981-06-11 | Teijin Ltd | Polymer bonding with albumin |
| FI76888C (fi) * | 1981-04-29 | 1988-12-12 | Ciba Geigy Ag | Nya medel och foerpackningar foer immunologiska analyser. |
| IL66094A0 (en) * | 1982-06-22 | 1982-09-30 | Yeda Res & Dev | Synthesis with multipolymer systems |
| US4595656A (en) * | 1984-01-06 | 1986-06-17 | Becton Dickinson & Company | Coupling agents and products produced therefrom |
| US4615985A (en) * | 1984-04-16 | 1986-10-07 | Genetic Diagnostics Corporation | Immobilized protein on nylon for immunoassay |
| WO1986002654A1 (en) * | 1984-10-29 | 1986-05-09 | Memtec Limited | Sulphuryl chloride/polyamide derivatives |
| US5108923A (en) * | 1986-04-25 | 1992-04-28 | Collaborative Research, Inc. | Bioadhesives for cell and tissue adhesion |
| 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 |
| ATE102074T1 (de) * | 1989-09-29 | 1994-03-15 | Rohm & Haas | Ligand enthaltendes medium fuer chromatographische trennung, verfahren zur dessen herstellung und dessen verwendung zur isolierung von synthetischen oder natuerlichen molekuelen von einer fluidmischung. |
| WO1992008790A1 (en) * | 1990-11-14 | 1992-05-29 | Cargill, Incorporated | Conjugates of poly(vinylsaccharide) with proteins for the stabilization of proteins |
| US5424219A (en) * | 1991-10-25 | 1995-06-13 | Cytech Biomedical, Inc. | Method of performing assays for biomolecules and solid supports for use in such methods |
| US6048735A (en) * | 1996-12-05 | 2000-04-11 | Idego Aps | Sensor laminates and multi-sectioned fluid delivery devices for detecting by immunoassay target molecules in biological fluids |
| US20160324269A1 (en) | 2015-05-08 | 2016-11-10 | Under Armour, Inc. | Footwear Including an Adaptable and Adjustable Lacing System |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1171774A (en) * | 1966-02-10 | 1969-11-26 | Dunlop Co Ltd | Improvements in and relating to Bonding. |
| US3639558A (en) * | 1968-02-19 | 1972-02-01 | Louis Csizmas | Immunological reagent particles having proteinaceous materials covalently bonded thereto |
| AT317424B (de) * | 1971-06-09 | 1974-08-26 | Boehringer Mannheim Gmbh | Verfahren zur Herstellung von trägergebundenen Proteinen |
| US3830699A (en) * | 1972-03-16 | 1974-08-20 | Exxon Research Engineering Co | Insolubilized enzymes |
| IL42516A (en) * | 1973-06-15 | 1976-11-30 | Mordechai Sokolovsky | Polyamides are converted by aldehyde and isonitrile groups and a process for their preparation |
| FR2234311B1 (OSRAM) * | 1973-06-21 | 1976-04-30 | Air Liquide | |
| GB1485122A (en) * | 1973-08-06 | 1977-09-08 | Nat Res Dev | Biologically active matrices |
| US3985617A (en) * | 1974-10-29 | 1976-10-12 | Ajinomoto Co., Inc. | Immobilization of biologically active proteins with a polypeptide azide |
| US4007089A (en) * | 1975-04-30 | 1977-02-08 | Nelson Research & Development Company | Method for binding biologically active compounds |
| US4045384A (en) * | 1976-07-23 | 1977-08-30 | The Dow Chemical Company | Method for forming an amide bond between a latex and protein |
-
1976
- 1976-01-29 DE DE2603319A patent/DE2603319C3/de not_active Expired
- 1976-11-24 AT AT872676A patent/AT359021B/de not_active IP Right Cessation
- 1976-12-13 CA CA267,721A patent/CA1087608A/en not_active Expired
- 1976-12-17 NL NL7614014A patent/NL7614014A/xx not_active Application Discontinuation
- 1976-12-17 IL IL51126A patent/IL51126A/xx unknown
- 1976-12-23 IT IT30848/76A patent/IT1065504B/it active
-
1977
- 1977-01-18 US US05/760,296 patent/US4119589A/en not_active Expired - Lifetime
- 1977-01-25 BE BE174350A patent/BE850717A/xx not_active IP Right Cessation
- 1977-01-25 FR FR7702049A patent/FR2339620A1/fr active Granted
- 1977-01-25 SE SE7700761A patent/SE7700761L/xx not_active Application Discontinuation
- 1977-01-26 GB GB3147/77A patent/GB1521243A/en not_active Expired
- 1977-01-26 CH CH94577A patent/CH626092A5/de not_active IP Right Cessation
- 1977-01-27 DD DD7700197116A patent/DD128404A5/xx unknown
- 1977-01-27 AU AU21737/77A patent/AU509729B2/en not_active Expired
- 1977-01-28 HU HU77BO1651A patent/HU176482B/hu unknown
- 1977-01-28 DK DK36377A patent/DK36377A/da not_active Application Discontinuation
- 1977-01-28 JP JP857577A patent/JPS5294489A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU2173777A (en) | 1978-08-03 |
| AT359021B (de) | 1980-10-10 |
| FR2339620A1 (fr) | 1977-08-26 |
| SE7700761L (sv) | 1977-07-30 |
| HU176482B (en) | 1981-03-28 |
| FR2339620B1 (OSRAM) | 1981-07-24 |
| DD128404A5 (de) | 1977-11-16 |
| US4119589A (en) | 1978-10-10 |
| AU509729B2 (en) | 1980-05-22 |
| GB1521243A (en) | 1978-08-16 |
| ATA872676A (de) | 1980-03-15 |
| BE850717A (fr) | 1977-07-25 |
| DE2603319C3 (de) | 1979-08-23 |
| IL51126A0 (en) | 1977-02-28 |
| NL7614014A (nl) | 1977-08-02 |
| IL51126A (en) | 1979-11-30 |
| IT1065504B (it) | 1985-02-25 |
| DK36377A (da) | 1977-07-30 |
| CH626092A5 (OSRAM) | 1981-10-30 |
| DE2603319A1 (de) | 1977-08-11 |
| DE2603319B2 (de) | 1978-12-21 |
| JPS5294489A (en) | 1977-08-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1087608A (en) | Method for immobilizing protein on a carrier | |
| US4182695A (en) | Polyamide-fixed biologically active protein | |
| CA1339251C (en) | Derivatized glass supports for peptide and protein sequencing | |
| Schmitt et al. | Synthesis and characterization of chelator-lipids for reversible immobilization of engineered proteins at self-assembled lipid interfaces | |
| EP0455905B1 (en) | Dipsticks for nucleic acid hybridization assays and methods for covalently immobilizing oligonucleotides | |
| US4694044A (en) | Adsorbent | |
| US5576220A (en) | Thin film HPMP matrix systems and methods for constructing and displaying ligands | |
| US3970597A (en) | Novel substituted polyamides and process for producing them | |
| US6602692B1 (en) | Method for immobilizing biomolecules and affinity ligands on polymer carriers | |
| Kallury et al. | Enhanced stability of urease immobilized onto phospholipid covalently bound to silica, tungsten, and fluoropolymer surfaces | |
| JPS6014028B2 (ja) | ヒドロキシ−スクシンイミド−エステル誘導体及びその製造法 | |
| JPS61164160A (ja) | ハイブリツド化分析による検出のための核酸の光化学的標識付け方法 | |
| Laursen | [30] Coupling techniques in solid-phase sequencing | |
| US4245064A (en) | Activated solid carrier and a method of its preparation | |
| JPH06199930A (ja) | 生物学的活性ポリマー | |
| KR100938777B1 (ko) | 다중 아민기를 갖는 펩티드 핵산과 이를 이용하는 핵산검출 장치 | |
| GB1571182A (en) | Carrier-bound biologically active substances and process for their manufacture | |
| EP2101174B1 (en) | Solid phases optimized for chemiluminescent detection | |
| KR100379720B1 (ko) | 덴드리머 단일층 지지체 및 그의 제조방법 | |
| KR100537400B1 (ko) | 아미노알킬트리알킬실릴 셀룰로오스 및 표면 코팅 방법 | |
| EP0123300A2 (en) | Complexing of biologically active or functional compounds and methods of preparing and utilizing same | |
| CN1291200A (zh) | 多孔聚合物珠状载体高分子材料的生产装置 | |
| KR20030009732A (ko) | 다중 아미노에틸 분자층으로 표면을 코팅한 유기 고분자기질 | |
| US4440903A (en) | Dihaloisocyanide derivatives of polymers for coupling nucleophiles | |
| SE442022B (sv) | Urokinasderivat bestaende av urokinas bundet till fibrinogen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |