DK172602B1 - Metalchelatharpikser, fremgangsmåde til fremstilling deraf, anvendelse deraf til metalchelat-chromatografi, nitrilotrieddik - Google Patents
Metalchelatharpikser, fremgangsmåde til fremstilling deraf, anvendelse deraf til metalchelat-chromatografi, nitrilotrieddik Download PDFInfo
- Publication number
- DK172602B1 DK172602B1 DK198702851A DK285187A DK172602B1 DK 172602 B1 DK172602 B1 DK 172602B1 DK 198702851 A DK198702851 A DK 198702851A DK 285187 A DK285187 A DK 285187A DK 172602 B1 DK172602 B1 DK 172602B1
- Authority
- DK
- Denmark
- Prior art keywords
- metal chelate
- proteins
- chelate resin
- cooh
- chromatography
- Prior art date
Links
- 239000011347 resin Substances 0.000 title claims abstract description 48
- 229920005989 resin Polymers 0.000 title claims abstract description 48
- 239000013522 chelant Substances 0.000 title claims abstract description 41
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 21
- 239000002184 metal Substances 0.000 title claims abstract description 21
- 238000004587 chromatography analysis Methods 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 9
- 235000021419 vinegar Nutrition 0.000 title 1
- 239000000052 vinegar Substances 0.000 title 1
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 22
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 22
- 239000011159 matrix material Substances 0.000 claims abstract description 14
- 125000006850 spacer group Chemical group 0.000 claims abstract description 8
- 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 claims description 14
- 229920000936 Agarose Polymers 0.000 claims description 13
- 238000000746 purification Methods 0.000 claims description 8
- SYFQYGMJENQVQT-UHFFFAOYSA-N 6-amino-2-[bis(carboxymethyl)amino]hexanoic acid Chemical compound NCCCCC(C(O)=O)N(CC(O)=O)CC(O)=O SYFQYGMJENQVQT-UHFFFAOYSA-N 0.000 claims description 5
- BQDYDULZSDRWMI-UHFFFAOYSA-N 4-amino-2-[bis(carboxymethyl)amino]butanoic acid Chemical compound NCCC(C(O)=O)N(CC(O)=O)CC(O)=O BQDYDULZSDRWMI-UHFFFAOYSA-N 0.000 claims description 4
- 238000001042 affinity chromatography Methods 0.000 claims description 4
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 4
- 150000002815 nickel Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000012266 salt solution Substances 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 241000220317 Rosa Species 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical group OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 abstract description 19
- 235000014304 histidine Nutrition 0.000 abstract 1
- 150000002411 histidines Chemical class 0.000 abstract 1
- 235000018102 proteins Nutrition 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- 229920002684 Sepharose Polymers 0.000 description 11
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 9
- 229910021645 metal ion Inorganic materials 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 108090000765 processed proteins & peptides Proteins 0.000 description 7
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910001453 nickel ion Inorganic materials 0.000 description 5
- 108010044467 Isoenzymes Proteins 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229920001222 biopolymer Polymers 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229960004198 guanidine Drugs 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910006148 NiII Inorganic materials 0.000 description 3
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 3
- 241000080590 Niso Species 0.000 description 3
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000001488 sodium phosphate Substances 0.000 description 3
- 229910000162 sodium phosphate Inorganic materials 0.000 description 3
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 3
- 102000018832 Cytochromes Human genes 0.000 description 2
- 108010052832 Cytochromes Proteins 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 102000004142 Trypsin Human genes 0.000 description 2
- 108090000631 Trypsin Proteins 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- KDJVUTSOHYQCDQ-UHFFFAOYSA-N carbamic acid;1h-imidazole Chemical group NC([O-])=O.[NH2+]1C=CN=C1 KDJVUTSOHYQCDQ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- TVMUHOAONWHJBV-UHFFFAOYSA-N dehydroglycine Chemical compound OC(=O)C=N TVMUHOAONWHJBV-UHFFFAOYSA-N 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000006167 equilibration buffer Substances 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 2
- 229910000363 nickel(II) sulfate Inorganic materials 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000012064 sodium phosphate buffer Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000012588 trypsin Substances 0.000 description 2
- YMVDHFYGOMPPIT-UHFFFAOYSA-N 2-[bis(carboxymethyl)amino]-4-(phenylmethoxycarbonylamino)butanoic acid Chemical compound OC(=O)CN(CC(O)=O)C(C(O)=O)CCNC(=O)OCC1=CC=CC=C1 YMVDHFYGOMPPIT-UHFFFAOYSA-N 0.000 description 1
- RKSASMXBVVMAAS-UHFFFAOYSA-N 2-[bis(carboxymethyl)amino]-6-(phenylmethoxycarbonylamino)hexanoic acid Chemical compound OC(=O)CN(CC(O)=O)C(C(O)=O)CCCCNC(=O)OCC1=CC=CC=C1 RKSASMXBVVMAAS-UHFFFAOYSA-N 0.000 description 1
- KXMSCBRTBLPGIN-UHFFFAOYSA-N 4-azaniumyl-2-(phenylmethoxycarbonylamino)butanoate Chemical compound NCCC(C(O)=O)NC(=O)OCC1=CC=CC=C1 KXMSCBRTBLPGIN-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 102000014914 Carrier Proteins Human genes 0.000 description 1
- 229910002476 CuII Inorganic materials 0.000 description 1
- -1 CuII ions Chemical class 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 102000003855 L-lactate dehydrogenase Human genes 0.000 description 1
- 108700023483 L-lactate dehydrogenases Proteins 0.000 description 1
- 108010052285 Membrane Proteins Proteins 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 108091008324 binding proteins Proteins 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-N bromoacetic acid Chemical compound OC(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000004648 butanoic acid derivatives Chemical class 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical class OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 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
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003398 denaturant Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000012149 elution buffer Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000003278 haem Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 150000002668 lysine derivatives Chemical class 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- UIVBYQGBSFLFCW-UHFFFAOYSA-N prop-1-ene-1,1-diamine Chemical compound CC=C(N)N UIVBYQGBSFLFCW-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/14—Extraction; Separation; Purification
- C07K1/16—Extraction; Separation; Purification by chromatography
- C07K1/22—Affinity chromatography or related techniques based upon selective absorption processes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/38—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 - B01D15/36
- B01D15/3804—Affinity chromatography
- B01D15/3828—Ligand exchange chromatography, e.g. complexation, chelation or metal interaction chromatography
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
- B01J20/3244—Non-macromolecular compounds
- B01J20/3265—Non-macromolecular compounds with an organic functional group containing a metal, e.g. a metal affinity ligand
Landscapes
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biophysics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Treatment Of Water By Ion Exchange (AREA)
- Developing Agents For Electrophotography (AREA)
- Peptides Or Proteins (AREA)
- Enzymes And Modification Thereof (AREA)
- Polymerisation Methods In General (AREA)
- Manufacture And Refinement Of Metals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH278286 | 1986-07-10 | ||
| CH278286 | 1986-07-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK285187D0 DK285187D0 (da) | 1987-06-03 |
| DK285187A DK285187A (da) | 1988-01-11 |
| DK172602B1 true DK172602B1 (da) | 1999-02-22 |
Family
ID=4241469
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK198702851A DK172602B1 (da) | 1986-07-10 | 1987-06-03 | Metalchelatharpikser, fremgangsmåde til fremstilling deraf, anvendelse deraf til metalchelat-chromatografi, nitrilotrieddik |
| DK199701493A DK172891B1 (da) | 1986-07-10 | 1997-12-19 | Fremgangsmåde til fremstilling af nitrilotrieddikesyrederivater |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK199701493A DK172891B1 (da) | 1986-07-10 | 1997-12-19 | Fremgangsmåde til fremstilling af nitrilotrieddikesyrederivater |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4877830A (xx) |
| EP (1) | EP0253303B1 (xx) |
| JP (2) | JPH0822382B2 (xx) |
| AT (1) | ATE76866T1 (xx) |
| AU (1) | AU596674B2 (xx) |
| CA (1) | CA1304886C (xx) |
| DE (1) | DE3779501D1 (xx) |
| DK (2) | DK172602B1 (xx) |
| IE (1) | IE60468B1 (xx) |
| IL (1) | IL83079A (xx) |
| NZ (1) | NZ220948A (xx) |
| PH (1) | PH23746A (xx) |
| ZA (1) | ZA874860B (xx) |
Families Citing this family (75)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1304886C (en) * | 1986-07-10 | 1992-07-07 | Heinz Dobeli | Metal chelate resins |
| US5057302A (en) * | 1987-02-13 | 1991-10-15 | Abbott Laboratories | Bifunctional chelating agents |
| CA1340522C (en) * | 1987-03-10 | 1999-05-04 | Heinz Dobeli | Fusion proteins containing neighbouring histidines for improved purification |
| US5225534A (en) * | 1987-09-08 | 1993-07-06 | Hoffmann-La Roche Inc. | Recombinant malarial polypeptides |
| EP0309746A1 (de) * | 1987-09-08 | 1989-04-05 | F. Hoffmann-La Roche Ag | Antimalaria-Vakzine |
| US4952321A (en) * | 1988-10-07 | 1990-08-28 | Brigham Young University | Process of removing and concentrating desired ions from solutions |
| US5169936A (en) * | 1989-04-14 | 1992-12-08 | Biogen, Inc. | Protein purification on immobilized metal affinity resins effected by elution using a weak ligand |
| ATE145010T1 (de) * | 1989-08-19 | 1996-11-15 | Qiagen Gmbh | Verfahren und vorrichtung zur trennung und detektion von komponenten eines stoffgemisches durch temperaturgradienten-gelelektrophorese |
| US5266686A (en) * | 1992-09-25 | 1993-11-30 | Pierce Chemical Company | Method for isolation and purification of enzyme-antibody conjugates |
| CA2125467C (en) * | 1993-07-06 | 2001-02-06 | Heinz Dobeli | Process for producing hydrophobic polypeptides, proteins or peptides |
| SE9303822D0 (sv) * | 1993-11-18 | 1993-11-18 | Kabi Pharmacia Ab | Method for purification |
| DE4433980C2 (de) * | 1994-09-23 | 1996-08-22 | Boehringer Ingelheim Int | Verfahren und Biosensorhit zur Untersuchung der Wechselwirkung von Biomolekülen mittels Oberflächen-Plasma-Resonanz |
| US6472148B1 (en) | 1994-09-26 | 2002-10-29 | President And Fellows Of Harvard College | Molecular recognition at surfaces derivatized with self-assembled monolayers |
| US5620850A (en) | 1994-09-26 | 1997-04-15 | President And Fellows Of Harvard College | Molecular recognition at surfaces derivatized with self-assembled monolayers |
| TW442492B (en) * | 1995-07-26 | 2001-06-23 | Novartis Ag | Process for the enrichment of interferon |
| DE19531173A1 (de) * | 1995-08-24 | 1997-02-27 | Boehringer Mannheim Gmbh | Verfahren zum Stabilisieren des Gehalts glykierten Proteins einer Probe auf einem Matrixmaterial |
| DE69730551T2 (de) | 1996-04-15 | 2005-09-01 | Givaudan S.A. | Hydroxyperoxide Lyasen |
| US5858724A (en) * | 1996-07-16 | 1999-01-12 | Pel-Freez | Recombinant rabbit tissue factor |
| US5962641A (en) * | 1996-08-16 | 1999-10-05 | Clontech Laboratories, Inc. | Method for purification of recombinant proteins |
| US7014992B1 (en) | 1996-11-05 | 2006-03-21 | Clinical Micro Sensors, Inc. | Conductive oligomers attached to electrodes and nucleoside analogs |
| DE19645729C1 (de) * | 1996-11-06 | 1998-06-04 | Brahms Diagnostica Gmbh | Rezeptorbindungsassay, für den Rezeptorbindungsassay geeigneter rekombinanter Fusionsrezeptor, Vektor zu dessen Herstellung sowie Reagenziensatz für die Durchführung des Rezeptorbindungsassays |
| AU748903B2 (en) * | 1997-06-24 | 2002-06-13 | Proteus Molecular Design Limited | Angiotensin derivatives |
| US6068993A (en) * | 1997-07-02 | 2000-05-30 | Biobras Sa | Vector for expression of heterologous protein and methods for extracting recombinant protein and for purifying isolated recombinant insulin |
| US7087148B1 (en) | 1998-06-23 | 2006-08-08 | Clinical Micro Sensors, Inc. | Binding acceleration techniques for the detection of analytes |
| CA2277372C (en) * | 1998-07-13 | 2011-03-15 | Tran Quang Minh | Affinity immobilised metal resins |
| ATE302940T1 (de) | 1999-03-04 | 2005-09-15 | Retsch Kurt Gmbh & Co Kg | Verfahren und vorrichtung zum aufschluss von biologischem material |
| US6479300B1 (en) | 1999-03-15 | 2002-11-12 | Millipore Corporation | Metal loaded ligand bound membranes for metal ion affinity chromatography |
| US7312087B2 (en) * | 2000-01-11 | 2007-12-25 | Clinical Micro Sensors, Inc. | Devices and methods for biochip multiplexing |
| US20020177135A1 (en) * | 1999-07-27 | 2002-11-28 | Doung Hau H. | Devices and methods for biochip multiplexing |
| JP2001029783A (ja) * | 1999-07-13 | 2001-02-06 | Tran Quang Minh | 親和性固定化金属樹脂 |
| EP1069131B1 (en) | 1999-07-15 | 2006-03-15 | Qiagen GmbH | Methods for separating particulate substrates from solution while minimizing particle loss |
| US6379708B1 (en) * | 1999-11-20 | 2002-04-30 | Cytologic, Llc | Method for enhancing immune responses in mammals |
| US6623655B1 (en) | 2000-04-24 | 2003-09-23 | Sigma-Aldrich Co. | Metal chelating compositions |
| GB0028879D0 (en) * | 2000-11-27 | 2001-01-10 | Prometic Biosciences Ltd | Adsorbents and their use |
| WO2003050540A2 (en) * | 2001-12-05 | 2003-06-19 | Large Scale Biology Corporation | Flexible method and apparatus for high throughput production and purification of multiple proteins |
| WO2003104814A2 (en) * | 2002-01-01 | 2003-12-18 | Phynexus, Inc. | Biomolecule open channel solid phase extraction systems and methods |
| US7122640B2 (en) * | 2002-06-10 | 2006-10-17 | Phynexus, Inc. | Open channel solid phase extraction systems and methods |
| US7151167B2 (en) * | 2002-06-10 | 2006-12-19 | Phynexus, Inc. | Open channel solid phase extraction systems and methods |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU426693B2 (en) * | 1968-07-18 | 1972-07-31 | Mobil Oil Corporation | Fuel additive |
| US4530963A (en) * | 1982-08-20 | 1985-07-23 | Devoe-Holbein International, N.V. | Insoluble chelating compositions |
| CA1304886C (en) * | 1986-07-10 | 1992-07-07 | Heinz Dobeli | Metal chelate resins |
-
1987
- 1987-06-02 CA CA000538559A patent/CA1304886C/en not_active Expired - Lifetime
- 1987-06-03 DK DK198702851A patent/DK172602B1/da not_active IP Right Cessation
- 1987-07-03 ZA ZA874860A patent/ZA874860B/xx unknown
- 1987-07-03 IL IL83079A patent/IL83079A/xx not_active IP Right Cessation
- 1987-07-03 NZ NZ220948A patent/NZ220948A/xx unknown
- 1987-07-06 AU AU75245/87A patent/AU596674B2/en not_active Expired
- 1987-07-07 PH PH35505A patent/PH23746A/en unknown
- 1987-07-08 EP EP87109892A patent/EP0253303B1/de not_active Expired - Lifetime
- 1987-07-08 DE DE8787109892T patent/DE3779501D1/de not_active Expired - Lifetime
- 1987-07-08 AT AT87109892T patent/ATE76866T1/de not_active IP Right Cessation
- 1987-07-09 IE IE184287A patent/IE60468B1/en not_active IP Right Cessation
- 1987-07-09 JP JP62169950A patent/JPH0822382B2/ja not_active Expired - Lifetime
- 1987-07-13 US US07/072,452 patent/US4877830A/en not_active Expired - Lifetime
-
1995
- 1995-06-23 JP JP7157981A patent/JP2562571B2/ja not_active Expired - Lifetime
-
1997
- 1997-12-19 DK DK199701493A patent/DK172891B1/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NZ220948A (en) | 1990-07-26 |
| DE3779501D1 (de) | 1992-07-09 |
| EP0253303A3 (en) | 1989-05-24 |
| ATE76866T1 (de) | 1992-06-15 |
| AU7524587A (en) | 1988-01-14 |
| US4877830A (en) | 1989-10-31 |
| JP2562571B2 (ja) | 1996-12-11 |
| DK172891B1 (da) | 1999-09-13 |
| IL83079A (en) | 1991-11-21 |
| ZA874860B (en) | 1988-01-11 |
| IE871842L (en) | 1988-01-10 |
| IE60468B1 (en) | 1994-07-13 |
| CA1304886C (en) | 1992-07-07 |
| JPH0899944A (ja) | 1996-04-16 |
| EP0253303A2 (de) | 1988-01-20 |
| DK285187D0 (da) | 1987-06-03 |
| IL83079A0 (en) | 1987-12-31 |
| EP0253303B1 (de) | 1992-06-03 |
| JPS6344947A (ja) | 1988-02-25 |
| DK149397A (da) | 1997-12-19 |
| AU596674B2 (en) | 1990-05-10 |
| JPH0822382B2 (ja) | 1996-03-06 |
| DK285187A (da) | 1988-01-11 |
| PH23746A (en) | 1989-11-03 |
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Legal Events
| Date | Code | Title | Description |
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| AHB | Application shelved due to non-payment | ||
| B1 | Patent granted (law 1993) | ||
| PUP | Patent expired |