KR20110028522A - 안정한 ｎａｄ/ｎａｄｈ 유도체 - Google Patents
안정한 ｎａｄ/ｎａｄｈ 유도체 Download PDFInfo
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- KR20110028522A KR20110028522A KR1020117002057A KR20117002057A KR20110028522A KR 20110028522 A KR20110028522 A KR 20110028522A KR 1020117002057 A KR1020117002057 A KR 1020117002057A KR 20117002057 A KR20117002057 A KR 20117002057A KR 20110028522 A KR20110028522 A KR 20110028522A
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- South Korea
- Prior art keywords
- independently
- enzyme
- dehydrogenase
- nad
- coenzyme
- Prior art date
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- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical class C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 title abstract description 25
- 108090000790 Enzymes Chemical class 0.000 claims abstract description 45
- 102000004190 Enzymes Human genes 0.000 claims abstract description 45
- 238000001514 detection method Methods 0.000 claims abstract description 21
- 239000005515 coenzyme Substances 0.000 claims description 38
- 238000012360 testing method Methods 0.000 claims description 34
- 108010050375 Glucose 1-Dehydrogenase Proteins 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000012491 analyte Substances 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- -1 coenzyme a compound Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 238000005259 measurement Methods 0.000 claims description 14
- 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 claims description 12
- 239000008103 glucose Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 7
- 102000003855 L-lactate dehydrogenase Human genes 0.000 claims description 7
- 108700023483 L-lactate dehydrogenases Proteins 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 7
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 6
- 102000004420 Creatine Kinase Human genes 0.000 claims description 6
- 108010042126 Creatine kinase Proteins 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 6
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 5
- 229930024421 Adenine Natural products 0.000 claims description 5
- 101150065749 Churc1 gene Proteins 0.000 claims description 5
- 102100038239 Protein Churchill Human genes 0.000 claims description 5
- 229960000643 adenine Drugs 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 230000001419 dependent effect Effects 0.000 claims description 4
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 3
- 101710088194 Dehydrogenase Proteins 0.000 claims description 3
- 108010024636 Glutathione Proteins 0.000 claims description 3
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 3
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 3
- 235000010323 ascorbic acid Nutrition 0.000 claims description 3
- 229960005070 ascorbic acid Drugs 0.000 claims description 3
- 239000011668 ascorbic acid Substances 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000001569 carbon dioxide Substances 0.000 claims description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
- 235000012000 cholesterol Nutrition 0.000 claims description 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 3
- 235000018417 cysteine Nutrition 0.000 claims description 3
- 229960002433 cysteine Drugs 0.000 claims description 3
- 235000019441 ethanol Nutrition 0.000 claims description 3
- 235000001727 glucose Nutrition 0.000 claims description 3
- 229960003180 glutathione Drugs 0.000 claims description 3
- 235000003969 glutathione Nutrition 0.000 claims description 3
- 235000011187 glycerol Nutrition 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 239000004310 lactic acid Substances 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- 239000001630 malic acid Substances 0.000 claims description 3
- 235000011090 malic acid Nutrition 0.000 claims description 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 3
- 229960001860 salicylate Drugs 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 108010050201 2-hydroxybutyrate dehydrogenase Proteins 0.000 claims description 2
- 108010021809 Alcohol dehydrogenase Proteins 0.000 claims description 2
- 102000007698 Alcohol dehydrogenase Human genes 0.000 claims description 2
- 108020005199 Dehydrogenases Proteins 0.000 claims description 2
- 101000892220 Geobacillus thermodenitrificans (strain NG80-2) Long-chain-alcohol dehydrogenase 1 Proteins 0.000 claims description 2
- 108010009384 L-Iditol 2-Dehydrogenase Proteins 0.000 claims description 2
- 108030000198 L-amino-acid dehydrogenases Proteins 0.000 claims description 2
- 108010026217 Malate Dehydrogenase Proteins 0.000 claims description 2
- 102000013460 Malate Dehydrogenase Human genes 0.000 claims description 2
- 102100026974 Sorbitol dehydrogenase Human genes 0.000 claims description 2
- 235000001014 amino acid Nutrition 0.000 claims description 2
- 210000001124 body fluid Anatomy 0.000 claims description 2
- 235000013305 food Nutrition 0.000 claims description 2
- 229930182470 glycoside Natural products 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000002351 wastewater Substances 0.000 claims description 2
- 229940093530 coenzyme a Drugs 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 238000005375 photometry Methods 0.000 claims 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 abstract description 69
- 229950006238 nadide Drugs 0.000 abstract description 48
- 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 abstract description 42
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate 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](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 abstract description 21
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 40
- 229940088598 enzyme Drugs 0.000 description 38
- 239000000203 mixture Substances 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 238000004809 thin layer chromatography Methods 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 230000000694 effects Effects 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 239000008367 deionised water Substances 0.000 description 14
- 229910021641 deionized water Inorganic materials 0.000 description 14
- 238000004821 distillation Methods 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 238000003556 assay Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 11
- 238000000862 absorption spectrum Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 239000008346 aqueous phase Substances 0.000 description 10
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- 239000012043 crude product Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
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- VKIGAWAEXPTIOL-UHFFFAOYSA-N 2-hydroxyhexanenitrile Chemical compound CCCCC(O)C#N VKIGAWAEXPTIOL-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 238000002189 fluorescence spectrum Methods 0.000 description 5
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- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 5
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
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- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 4
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- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 3
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- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 3
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- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 3
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- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
- C12Q1/32—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase involving dehydrogenase
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- G—PHYSICS
- G01—MEASURING; TESTING
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- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
- G01N33/533—Production of labelled immunochemicals with fluorescent label
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| US7553615B2 (en) * | 2005-07-28 | 2009-06-30 | Roche Diagnostics Operations, Inc. | Compounds, methods, complexes, apparatuses and uses relating to stabile forms of NAD/NADH |
| DE102005035461A1 (de) * | 2005-07-28 | 2007-02-15 | Roche Diagnostics Gmbh | Stabile NAD/NADH-Derivate |
| EP2022859A1 (de) * | 2007-08-01 | 2009-02-11 | Roche Diagnostics GmbH | Verfahren und Vorrichtung zur Bestimmung der Konzentration eines Analyten mittels Fluoreszenzmessung |
| CN101497638B (zh) * | 2008-01-30 | 2012-09-26 | 中国科学院大连化学物理研究所 | 一种nad+类似物及其合成和应用 |
| EP2093284A1 (de) | 2008-02-19 | 2009-08-26 | F.Hoffmann-La Roche Ag | Stabilisierung von Dehydrogenasen mit stabilen Coenzymen |
| KR20130127555A (ko) | 2009-02-19 | 2013-11-22 | 에프. 호프만-라 로슈 아게 | 건식 화학 층에서 낮은 활성을 갖는 효소의 고속 반응 속도 |
| EP2226007A1 (de) | 2009-02-19 | 2010-09-08 | Roche Diagnostics GmbH | Testelementmagazin mit abgedeckten Testfeldern |
| EP2398388B1 (de) * | 2009-02-19 | 2020-04-08 | Roche Diabetes Care GmbH | Platzsparende magazinierung analytischer hilfsmittel |
| EP2226008A1 (de) | 2009-02-19 | 2010-09-08 | Roche Diagnostics GmbH | Verfahren zur Herstellung eines analytischen Magazins |
| EP2398909B1 (de) | 2009-02-19 | 2015-07-22 | F. Hoffmann-La Roche AG | Schnelle reaktionskinetik von enzymen mit niedriger aktivität in trockenen chemieschichten |
| ES2425631T3 (es) | 2009-07-27 | 2013-10-16 | F. Hoffmann-La Roche Ag | Síntesis enzimática de carba-NAD |
| JP5542931B2 (ja) * | 2009-07-27 | 2014-07-09 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | Ｎ置換ピリジニウム化合物の調製のための方法及び物質 |
| JP5544423B2 (ja) | 2009-07-27 | 2014-07-09 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | Ｎ置換ピリジニウム化合物の調製のための方法及び物質 |
| EP2292751A1 (de) * | 2009-08-20 | 2011-03-09 | Roche Diagnostics GmbH | Stabilisierung von Enzymen mit stabilen Coenzymen |
| EP2287605A1 (de) * | 2009-08-20 | 2011-02-23 | Roche Diagnostics GmbH | Vereinfachte Magazinierung integrierter Systeme |
| EP2333544A1 (de) | 2009-12-11 | 2011-06-15 | F. Hoffmann-La Roche AG | Sterilisierbare Chemie für Testelemente |
| CN102741694B (zh) | 2009-12-16 | 2014-12-24 | 霍夫曼-拉罗奇有限公司 | 借助于受保护的分析物的控释来检测测试元件中酶的分解 |
| KR101252351B1 (ko) * | 2010-05-24 | 2013-04-08 | 동국대학교 산학협력단 | 전기효소적 합성 반응을 위한 ｎａｄ(ｐ) 유도체의 전기화학적 환원 방법 |
| CN102453067B (zh) * | 2010-10-29 | 2015-08-05 | 中国科学院大连化学物理研究所 | 一种nad+类似物的制备方法及其应用 |
| EP2668161B1 (en) | 2011-01-26 | 2014-11-26 | Roche Diagniostics GmbH | Method and substances for preparation of n-substituted pyridinium compounds |
| EP2696764B1 (de) | 2011-04-12 | 2015-10-14 | Roche Diagnostics GmbH | Analytisches hilfsmittel |
| US9752990B2 (en) | 2013-09-30 | 2017-09-05 | Honeywell International Inc. | Low-powered system for driving a fuel control mechanism |
| CN102863495A (zh) * | 2011-07-06 | 2013-01-09 | 上海执诚生物科技股份有限公司 | 一种含有nad+或nadh的稳定的组合物 |
| MX2014003415A (es) | 2011-09-28 | 2014-04-10 | Hoffmann La Roche | Mediadores azo. |
| JP6128808B2 (ja) * | 2011-11-15 | 2017-05-17 | 栄研化学株式会社 | 酵素活性の検出、測定方法およびこれを利用したキット |
| EP2620507A1 (en) | 2012-01-25 | 2013-07-31 | Roche Diagnostics GmbH | Method for the evaluation of the quality of a test element |
| EP2636750A1 (en) | 2012-03-06 | 2013-09-11 | Roche Diagniostics GmbH | Compatible solute ectoine as well as derivatives thereof for enzyme stabilization |
| WO2013156526A1 (de) | 2012-04-19 | 2013-10-24 | F. Hoffmann-La Roche Ag | Verfahren und vorrichtung zur bestimmung einer analytkonzentration in blut |
| US8921061B2 (en) * | 2012-11-02 | 2014-12-30 | Roche Diagnostics Operations, Inc. | Reagent materials and associated test elements |
| US8920628B2 (en) | 2012-11-02 | 2014-12-30 | Roche Diagnostics Operations, Inc. | Systems and methods for multiple analyte analysis |
| CN104854457B (zh) | 2012-12-20 | 2016-09-14 | 霍夫曼-拉罗奇有限公司 | 用于分析体液样本的方法 |
| JP6462585B2 (ja) | 2012-12-20 | 2019-01-30 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 医学的測定曲線の評価方法 |
| EP2770064A1 (de) | 2013-02-22 | 2014-08-27 | F. Hoffmann-La Roche AG | Hocheffiziente Herstellung von Blutglucose-Teststreifen |
| EP2781919A1 (en) | 2013-03-19 | 2014-09-24 | Roche Diagniostics GmbH | Method / device for generating a corrected value of an analyte concentration in a sample of a body fluid |
| WO2014180939A1 (en) | 2013-05-08 | 2014-11-13 | Roche Diagnostics Gmbh | Stabilization of enzymes by nicotinic acid |
| HK1213296A1 (zh) * | 2013-06-04 | 2016-06-30 | 豪夫迈‧罗氏有限公司 | 用於fret的新化合物及与其相关的方法 |
| EP2811299A1 (en) | 2013-06-07 | 2014-12-10 | Roche Diagniostics GmbH | Test element for detecting at least one analyte in a body fluid |
| WO2015063025A1 (en) | 2013-10-29 | 2015-05-07 | F. Hoffmann-La Roche Ag | Nano-enzyme containers for test elements |
| EP3074524B1 (en) | 2013-11-27 | 2019-11-06 | Roche Diabetes Care GmbH | Composition comprising up-converting phosphors for detecting an analyte |
| EP2927319A1 (en) | 2014-03-31 | 2015-10-07 | Roche Diagnostics GmbH | High load enzyme immobilization by crosslinking |
| JP6522003B2 (ja) | 2014-04-14 | 2019-05-29 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | フェナジニウムメディエーター |
| WO2016022604A2 (en) * | 2014-08-05 | 2016-02-11 | Becton Dickinson And Company | Methods and compositions for analyzing glucose-6-phosphate dehydrogenase activity in blood samples |
| WO2016026959A1 (en) | 2014-08-22 | 2016-02-25 | Roche Diagnostics Gmbh | Redoxindicators |
| KR101950615B1 (ko) | 2014-08-25 | 2019-02-20 | 에프. 호프만-라 로슈 아게 | 간섭을 보상하는 두 개의 전극들의 테스트 스트립 |
| BR112018012665A2 (pt) | 2015-12-21 | 2018-12-04 | Hoffmann La Roche | 3-hidroxibutirato desidrogenase mutante de alcaligenes faecalis, ácido nucleico, célula, método para determinar a quantidade ou concentração de 3-hidroxibutirato, uso da 3-hbdh mutante e dispositivo |
| WO2017137491A1 (en) | 2016-02-09 | 2017-08-17 | Roche Diabetes Care Gmbh | Mutant 3-hydroxybutyrate dehydrogenase from rhodobacter sphaeroides as well as methods and uses involving the same |
| EP4481375A3 (en) | 2016-10-05 | 2025-04-02 | F. Hoffmann-La Roche AG | Detection reagents and electrode arrangements for multi-analyte diagnostic test elements, as well as methods of using the same |
| EP3339431A1 (en) | 2016-12-22 | 2018-06-27 | Roche Diabetes Care GmbH | Glucose dehydrogenase variants with improved properties |
| CN107966555A (zh) * | 2017-11-23 | 2018-04-27 | 中山市创艺生化工程有限公司 | 一种用于稳定保存nad或其衍生物的存储液 |
| RU2754453C1 (ru) | 2018-02-28 | 2021-09-02 | Ф. Хоффманн-Ля Рош Аг | Обеспечивающее биосовместимость покрытие для непрерывного измерения аналита |
| CN111217744A (zh) * | 2018-11-26 | 2020-06-02 | 中国科学院大连化学物理研究所 | 一种d-氨基酸基nad+类似物及其合成和应用 |
| WO2022132963A1 (en) | 2020-12-15 | 2022-06-23 | Abbott Diabetes Care Inc. | Nad(p) depot for nad(p)-dependent enzyme-based sensors |
| WO2025245355A1 (en) | 2024-05-24 | 2025-11-27 | Abbott Diabetes Care Inc. | Dispensed area and drop solid content tunability |
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| JPS53107486A (en) * | 1977-02-28 | 1978-09-19 | Wako Pure Chem Ind Ltd | Stabilized nadh aqueous solution |
| JPS61274636A (ja) | 1985-05-30 | 1986-12-04 | 西南自動車工業株式会社 | 活魚水槽 |
| US5801006A (en) * | 1997-02-04 | 1998-09-01 | Specialty Assays, Inc. | Use of NADPH and NADH analogs in the measurement of enzyme activities and metabolites |
| JP4260245B2 (ja) * | 1998-06-25 | 2009-04-30 | 株式会社三菱化学ヤトロン | 還元型ニコチンアミドアデニンジヌクレオチド類の分解を防止する方法及び分解防止用試薬 |
| US6380380B1 (en) | 1999-01-04 | 2002-04-30 | Specialty Assays, Inc. | Use of nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucliotide phosphate (NADP) analogs to measure enzyme activities metabolites and substrates |
| WO2001094370A1 (en) | 2000-06-07 | 2001-12-13 | Wako Pure Chemical Industries, Ltd. | Coenzyme derivatives and enzymes appropriate therefor |
| KR101002194B1 (ko) | 2002-05-16 | 2011-01-13 | 에프. 호프만-라 로슈 아게 | 중합체 층의 제조 방법 |
| DE10221845A1 (de) | 2002-05-16 | 2003-11-27 | Roche Diagnostics Gmbh | Verfahren und Reagenzsystem mit nicht-regenerierbarem Enzym-Coenzym-Komplex |
| DE102005035461A1 (de) * | 2005-07-28 | 2007-02-15 | Roche Diagnostics Gmbh | Stabile NAD/NADH-Derivate |
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