CS204190B1 - Activation method for hydrxyl groups containing insoluble carriers - Google Patents

Activation method for hydrxyl groups containing insoluble carriers Download PDF

Info

Publication number: CS204190B1
Authority: CS; Czechoslovakia
Prior art keywords: activated; group; carrier; trichlorophenyl; groups
Prior art date: 1978-02-22

Application number

CS781125A

Other languages

Czech (cs)

English (en)

Inventor

Jaroslav Drobnik

Jaroslav Kalal

Jiri Labsky

Vladimir Saudek

Frantisek Svec

Original Assignee

Jaroslav Drobnik

Jaroslav Kalal

Jiri Labsky

Vladimir Saudek

Frantisek Svec

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.)

1978-02-22

Filing date

1978-02-22

Publication date

1981-03-31

1978-02-22 Application filed by Jaroslav Drobnik, Jaroslav Kalal, Jiri Labsky, Vladimir Saudek, Frantisek Svec filed Critical Jaroslav Drobnik

1978-02-22 Priority to CS781125A priority Critical patent/CS204190B1/cs

1979-02-12 Priority to US06/011,428 priority patent/US4245064A/en

1979-02-14 Priority to GB7905229A priority patent/GB2015553B/en

1979-02-15 Priority to SE7901349A priority patent/SE7901349L/

1979-02-20 Priority to DD79211127A priority patent/DD143262A1/de

1979-02-21 Priority to FR7904415A priority patent/FR2418245A1/fr

1979-02-22 Priority to DE19792906989 priority patent/DE2906989A1/de

1981-03-31 Publication of CS204190B1 publication Critical patent/CS204190B1/cs

Links

238000000034 method Methods 0.000 title claims abstract description 33
230000004913 activation Effects 0.000 title claims description 11
239000000969 carrier Substances 0.000 title claims description 10
-1 dinitrophenyl Chemical group 0.000 claims abstract description 27
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
239000003446 ligand Substances 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 10
238000005406 washing Methods 0.000 claims description 8
230000008569 process Effects 0.000 claims description 7
150000001540 azides Chemical class 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
150000001718 carbodiimides Chemical class 0.000 claims description 5
238000006193 diazotization reaction Methods 0.000 claims description 5
125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 claims description 3
SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 2
238000002360 preparation method Methods 0.000 abstract description 9
150000002148 esters Chemical class 0.000 abstract description 8
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 abstract description 3
150000004676 glycans Chemical group 0.000 abstract description 3
229920001282 polysaccharide Polymers 0.000 abstract description 3
239000005017 polysaccharide Substances 0.000 abstract description 3
230000000269 nucleophilic effect Effects 0.000 abstract description 2
229920001568 phenolic resin Chemical group 0.000 abstract 2
229920002401 polyacrylamide Chemical group 0.000 abstract 2
229920000058 polyacrylate Chemical group 0.000 abstract 2
125000006501 nitrophenyl group Chemical group 0.000 abstract 1
229920000642 polymer Polymers 0.000 abstract 1
239000007787 solid Substances 0.000 abstract 1
230000000694 effects Effects 0.000 description 20
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
102000004142 Trypsin Human genes 0.000 description 10
108090000631 Trypsin Proteins 0.000 description 10
239000000047 product Substances 0.000 description 10
239000012588 trypsin Substances 0.000 description 10
NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 9
OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 8
239000001913 cellulose Substances 0.000 description 7
229920002678 cellulose Polymers 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
125000003277 amino group Chemical group 0.000 description 5
239000000872 buffer Substances 0.000 description 5
230000008878 coupling Effects 0.000 description 5
238000010168 coupling process Methods 0.000 description 5
238000005859 coupling reaction Methods 0.000 description 5
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
229920002134 Carboxymethyl cellulose Polymers 0.000 description 4
239000001768 carboxy methyl cellulose Substances 0.000 description 4
235000010948 carboxy methyl cellulose Nutrition 0.000 description 4
239000008112 carboxymethyl-cellulose Substances 0.000 description 4
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 4
229940104302 cytosine Drugs 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
229920000936 Agarose Polymers 0.000 description 3
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
150000004982 aromatic amines Chemical class 0.000 description 3
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 3
229920001577 copolymer Polymers 0.000 description 3
239000005457 ice water Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
150000007523 nucleic acids Chemical class 0.000 description 3
102000039446 nucleic acids Human genes 0.000 description 3
108020004707 nucleic acids Proteins 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
125000006850 spacer group Chemical group 0.000 description 3
LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
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 2
108010073038 Penicillin Amidase Proteins 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
229920002684 Sepharose Polymers 0.000 description 2
239000008351 acetate buffer Substances 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000009471 action Effects 0.000 description 2
230000003213 activating effect Effects 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
239000000427 antigen Substances 0.000 description 2
102000036639 antigens Human genes 0.000 description 2
108091007433 antigens Proteins 0.000 description 2
230000008901 benefit Effects 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000008103 glucose Substances 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
125000005647 linker group Chemical group 0.000 description 2
239000002609 medium Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
102000004196 processed proteins & peptides Human genes 0.000 description 2
108090000765 processed proteins & peptides Proteins 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
239000000725 suspension Substances 0.000 description 2
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
UJKKXYOMNWBXRY-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) carbonochloridate Chemical compound ClC(=O)OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl UJKKXYOMNWBXRY-UHFFFAOYSA-N 0.000 description 1
KUZDOAWPCGDGRN-UHFFFAOYSA-N (2,4,6-trichlorophenyl) carbonochloridate Chemical compound ClC(=O)OC1=C(Cl)C=C(Cl)C=C1Cl KUZDOAWPCGDGRN-UHFFFAOYSA-N 0.000 description 1
LGKWKOXFJWFQLI-UHFFFAOYSA-N (2,4-dinitrophenyl) formate Chemical compound [O-][N+](=O)C1=CC=C(OC=O)C([N+]([O-])=O)=C1 LGKWKOXFJWFQLI-UHFFFAOYSA-N 0.000 description 1
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
LZKGFGLOQNSMBS-UHFFFAOYSA-N 4,5,6-trichlorotriazine Chemical compound ClC1=NN=NC(Cl)=C1Cl LZKGFGLOQNSMBS-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
108010093096 Immobilized Enzymes Proteins 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
101710126321 Pancreatic trypsin inhibitor Proteins 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
229910003074 TiCl4 Inorganic materials 0.000 description 1
229920004890 Triton X-100 Polymers 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
238000001261 affinity purification Methods 0.000 description 1
125000003172 aldehyde group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
HVZMEJKDXFWCMF-UHFFFAOYSA-N aziridine oxirane Chemical compound N1CC1.O1CC1 HVZMEJKDXFWCMF-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GRDMQWRBLJZFML-UHFFFAOYSA-N bis(4-nitrophenyl) sulfite Chemical compound C1=CC([N+](=O)[O-])=CC=C1OS(=O)OC1=CC=C([N+]([O-])=O)C=C1 GRDMQWRBLJZFML-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
230000007423 decrease Effects 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
MMSVBKQTXSDWQN-UHFFFAOYSA-N ethyl 6-aminohexanoate;hydron;chloride Chemical compound Cl.CCOC(=O)CCCCCN MMSVBKQTXSDWQN-UHFFFAOYSA-N 0.000 description 1
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
230000001900 immune effect Effects 0.000 description 1
238000011534 incubation Methods 0.000 description 1
150000002527 isonitriles Chemical class 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical class C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
KGCNHWXDPDPSBV-UHFFFAOYSA-N p-nitrobenzyl chloride Chemical group [O-][N+](=O)C1=CC=C(CCl)C=C1 KGCNHWXDPDPSBV-UHFFFAOYSA-N 0.000 description 1
230000003071 parasitic effect Effects 0.000 description 1
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229920001184 polypeptide Polymers 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/02—Alkyl or cycloalkyl ethers
- C08B11/04—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals
- C08B11/14—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals with nitrogen-containing groups
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0036—Galactans; Derivatives thereof
- C08B37/0039—Agar; Agarose, i.e. D-galactose, 3,6-anhydro-D-galactose, methylated, sulfated, e.g. from the red algae Gelidium and Gracilaria; Agaropectin; Derivatives thereof, e.g. Sepharose, i.e. crosslinked agarose
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
- 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
- C12N11/091—Phenol resins; Amino resins
- 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
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2810/00—Chemical modification of a polymer
- C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently

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Chemical & Material Sciences (AREA)
Health & Medical 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)
Polymers & Plastics (AREA)
Biotechnology (AREA)
Biomedical Technology (AREA)
Microbiology (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Materials Engineering (AREA)
Molecular Biology (AREA)
General Chemical & Material Sciences (AREA)
Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Peptides Or Proteins (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CS781125A 1978-02-22 1978-02-22 Activation method for hydrxyl groups containing insoluble carriers CS204190B1 (en)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
CS781125A CS204190B1 (en)	1978-02-22	1978-02-22	Activation method for hydrxyl groups containing insoluble carriers
US06/011,428 US4245064A (en)	1978-02-22	1979-02-12	Activated solid carrier and a method of its preparation
GB7905229A GB2015553B (en)	1978-02-22	1979-02-14	Activated solid polymeric carrier and a method of its preparation
SE7901349A SE7901349L (sv)	1978-02-22	1979-02-15	Aktiverad fast berare och sett att framstella densamma
DD79211127A DD143262A1 (de)	1978-02-22	1979-02-20	Verfahren zur herstellung eines polymeren,zur bindung von nucleophilen gruppen aktivierten traegers
FR7904415A FR2418245A1 (fr)	1978-02-22	1979-02-21	Support solide active et procede pour sa fabrication
DE19792906989 DE2906989A1 (de)	1978-02-22	1979-02-22	Aktivierter fester traeger und seine herstellung

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CS781125A CS204190B1 (en)	1978-02-22	1978-02-22	Activation method for hydrxyl groups containing insoluble carriers

Publications (1)

Publication Number	Publication Date
CS204190B1 true CS204190B1 (en)	1981-03-31

Family

ID=5344814

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS781125A CS204190B1 (en)	1978-02-22	1978-02-22	Activation method for hydrxyl groups containing insoluble carriers

Country Status (7)

Country	Link
US (1)	US4245064A (de)
CS (1)	CS204190B1 (de)
DD (1)	DD143262A1 (de)
DE (1)	DE2906989A1 (de)
FR (1)	FR2418245A1 (de)
GB (1)	GB2015553B (de)
SE (1)	SE7901349L (de)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE7907035L (sv) *	1979-08-23	1981-02-24	Berbel Hegerdal	Forfarande for framstellning av flytande brensle ur biologiska ravaror
JPS56115727A (en) *	1980-02-19	1981-09-11	Kuraray Co Ltd	Carrier for immobilizing physiologically active substance
IT1209419B (it) *	1980-07-01	1989-07-16	Texcontor Ets	Composti ad attivita' mucolitica non assimilabili, processo per laloro preparazione e composizioni terapeutiche che li comprendono come principio attivo.
US4363634A (en) *	1980-07-18	1982-12-14	Akzona Incorporated	Glass support coated with synthetic polymer for bioprocess
US4357142A (en) *	1980-07-18	1982-11-02	Akzona Incorporated	Glass support coated with synthetic polymer for bioprocess
US4526690A (en) *	1983-02-04	1985-07-02	Millipore Corporation	Apparatus for nucleic acid quantification
DE3527909A1 (de) *	1985-08-03	1987-02-12	Basf Ag	Polymerisate mit aminogruppen, deren herstellung und verwendung
US4886836A (en) *	1987-06-03	1989-12-12	Pall Corporation	Activated medium with low non-specific protein adsorption
WO1990013540A1 (en) †	1989-04-19	1990-11-15	Enzon, Inc.	Active carbonates of polyalkylene oxides for modification of polypeptides
GB2267502B (en) *	1992-05-28	1997-01-22	Aligena Ag	Polymeric reaction products for use in immobilized buffered gels and membranes
WO1995012624A1 (fr) *	1993-11-05	1995-05-11	Elf Atochem S.A.	Materiau d'emballage ayant des proprietes barrieres a l'oxygene
US20030212022A1 (en) *	2001-03-23	2003-11-13	Jean-Marie Vogel	Compositions and methods for gene therapy
ES2254042T3 (es) *	2000-03-24	2008-03-16	Biosphere Medical, Inc.	Microesferas para embolizacion activa.
AT500669B1 (de)	2001-09-24	2007-02-15	Oesterr Forsch Seibersdorf	Fester träger zur immobilisierung von biomolekülen
US7770085B2 (en) *	2001-09-26	2010-08-03	Siemens Aktiengesellschaft	Replacement messages for identifying and preventing errors during the transmission of real time-critical data
MXPA05011159A (es) *	2003-04-14	2006-05-25	Pathogen Removal And Diagnosti	Metodo para identificar ligandos especificos para isoformas estructurales de proteinas.
US7964380B2 (en) *	2005-01-21	2011-06-21	Argylia Technologies	Nanoparticles for manipulation of biopolymers and methods of thereof
US8226926B2 (en)	2005-05-09	2012-07-24	Biosphere Medical, S.A.	Compositions and methods using microspheres and non-ionic contrast agents

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1289548A (de) *	1969-12-18	1972-09-20
US3879353A (en) *	1971-09-01	1975-04-22	Owens Illinois Inc	Linear copolymers having pendant peroxycarbonate ester functionality, their synthesis and use
US3959078A (en) *	1973-05-18	1976-05-25	Midwest Research Institute	Enzyme immobilization with a thermochemical-photochemical bifunctional agent
US3873514A (en) *	1974-05-17	1975-03-25	Bio Rad Laboratories	Preparation of gel for affinity chromatography
US4101721A (en) *	1976-12-09	1978-07-18	Wisconsin Alumni Research Foundation	Solid phase synthesis of protected peptides
US4090919A (en) *	1976-01-29	1978-05-23	Tanabe Seiyaku Co., Ltd.	Water-insoluble tannin preparation for immobilization of proteins
SE431758B (sv) *	1977-03-04	1984-02-27	Pharmacia Fine Chemicals Ab	Som tioleringsreagens eller berarmatris for enzymer anvendbart derivat av en sh-grupphaltig polymer

1978
- 1978-02-22 CS CS781125A patent/CS204190B1/cs unknown
1979
- 1979-02-12 US US06/011,428 patent/US4245064A/en not_active Expired - Lifetime
- 1979-02-14 GB GB7905229A patent/GB2015553B/en not_active Expired
- 1979-02-15 SE SE7901349A patent/SE7901349L/ not_active Application Discontinuation
- 1979-02-20 DD DD79211127A patent/DD143262A1/de not_active IP Right Cessation
- 1979-02-21 FR FR7904415A patent/FR2418245A1/fr not_active Withdrawn
- 1979-02-22 DE DE19792906989 patent/DE2906989A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
DD143262A1 (de)	1980-08-13
US4245064A (en)	1981-01-13
GB2015553B (en)	1982-09-29
SE7901349L (sv)	1979-08-23
DE2906989A1 (de)	1979-10-31
GB2015553A (en)	1979-09-12
FR2418245A1 (fr)	1979-09-21

Publication	Publication Date	Title
CS204190B1 (en)	1981-03-31	Activation method for hydrxyl groups containing insoluble carriers
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