ZA200210128B - Method comprising the indirect electrochemical regeneration of NAD(P)H. - Google Patents
Method comprising the indirect electrochemical regeneration of NAD(P)H. Download PDFInfo
- Publication number
- ZA200210128B ZA200210128B ZA200210128A ZA200210128A ZA200210128B ZA 200210128 B ZA200210128 B ZA 200210128B ZA 200210128 A ZA200210128 A ZA 200210128A ZA 200210128 A ZA200210128 A ZA 200210128A ZA 200210128 B ZA200210128 B ZA 200210128B
- Authority
- ZA
- South Africa
- Prior art keywords
- nad
- oxidation
- concentration
- oxygen
- monooxygenase
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 55
- 238000011069 regeneration method Methods 0.000 title claims abstract description 40
- 230000008929 regeneration Effects 0.000 title claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 50
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 37
- 239000001301 oxygen Substances 0.000 claims abstract description 37
- 239000000758 substrate Substances 0.000 claims abstract description 33
- 108010074633 Mixed Function Oxygenases Proteins 0.000 claims abstract description 17
- 102000008109 Mixed Function Oxygenases Human genes 0.000 claims abstract description 17
- 230000002255 enzymatic effect Effects 0.000 claims abstract description 17
- 108010053948 2-hydroxybiphenyl 3-monooxygenase Proteins 0.000 claims abstract description 15
- -1 2,3-dihydroxyphenyl Chemical class 0.000 claims abstract description 14
- 230000002829 reductive effect Effects 0.000 claims abstract description 11
- 238000006894 reductive elimination reaction Methods 0.000 claims abstract description 6
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 37
- 238000007254 oxidation reaction Methods 0.000 claims description 33
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims description 29
- 230000003647 oxidation Effects 0.000 claims description 28
- 239000010948 rhodium Substances 0.000 claims description 26
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound 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 claims description 25
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 23
- 229910052703 rhodium Inorganic materials 0.000 claims description 15
- 230000009467 reduction Effects 0.000 claims description 13
- 230000001590 oxidative effect Effects 0.000 claims description 10
- 102000016938 Catalase Human genes 0.000 claims description 9
- 108010053835 Catalase Proteins 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 238000005805 hydroxylation reaction Methods 0.000 claims description 7
- 239000012429 reaction media Substances 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229910021607 Silver chloride Inorganic materials 0.000 claims description 5
- 230000002051 biphasic effect Effects 0.000 claims description 5
- 230000001419 dependent effect Effects 0.000 claims description 5
- 230000033444 hydroxylation Effects 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 claims description 5
- 238000006220 Baeyer-Villiger oxidation reaction Methods 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 4
- 238000006735 epoxidation reaction Methods 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002097 pentamethylcyclopentadienyl group Chemical group 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 238000006757 chemical reactions by type Methods 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 229910052711 selenium Inorganic materials 0.000 claims description 3
- 239000011669 selenium Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000006213 oxygenation reaction Methods 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 5
- 102000004190 Enzymes Human genes 0.000 description 23
- 108090000790 Enzymes Proteins 0.000 description 23
- 230000015572 biosynthetic process Effects 0.000 description 20
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 8
- 239000000872 buffer Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 5
- 230000002411 adverse Effects 0.000 description 5
- YKOQAAJBYBTSBS-UHFFFAOYSA-N biphenyl-2,3-diol Chemical compound OC1=CC=CC(C=2C=CC=CC=2)=C1O YKOQAAJBYBTSBS-UHFFFAOYSA-N 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- ACFIXJIJDZMPPO-NNYOXOHSSA-N NADPH Chemical compound 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](OP(O)(O)=O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 ACFIXJIJDZMPPO-NNYOXOHSSA-N 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- 235000010292 orthophenyl phenol Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012431 aqueous reaction media Substances 0.000 description 3
- 229910001882 dioxygen Inorganic materials 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- IHPYMWDTONKSCO-UHFFFAOYSA-N 2,2'-piperazine-1,4-diylbisethanesulfonic acid Chemical compound OS(=O)(=O)CCN1CCN(CCS(O)(=O)=O)CC1 IHPYMWDTONKSCO-UHFFFAOYSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 101710163168 Flavin-dependent monooxygenase Proteins 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- 239000007990 PIPES buffer Substances 0.000 description 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
- 101710091169 Thiol-specific monooxygenase Proteins 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- FVTCRASFADXXNN-SCRDCRAPSA-N flavin mononucleotide Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-SCRDCRAPSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000036284 oxygen consumption Effects 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000008057 potassium phosphate buffer Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BFZHCUBIASXHPK-ODYOLWGQSA-N 11a-Hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC(C(=O)C)[C@@]1(C)C[C@H]2O BFZHCUBIASXHPK-ODYOLWGQSA-N 0.000 description 1
- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical compound OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 description 1
- UPXZHXVOMCGZDS-UHFFFAOYSA-N 2-phenylbenzene-1,3-diol Chemical group OC1=CC=CC(O)=C1C1=CC=CC=C1 UPXZHXVOMCGZDS-UHFFFAOYSA-N 0.000 description 1
- 102100031126 6-phosphogluconolactonase Human genes 0.000 description 1
- 108010029731 6-phosphogluconolactonase Proteins 0.000 description 1
- MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 1
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 1
- 102000018832 Cytochromes Human genes 0.000 description 1
- 108010052832 Cytochromes Proteins 0.000 description 1
- YPZRHBJKEMOYQH-UYBVJOGSSA-N FADH2 Chemical compound C1=NC2=C(N)N=CN=C2N1[C@@H]([C@H](O)[C@@H]1O)O[C@@H]1COP(O)(=O)OP(O)(=O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C(NC(=O)NC2=O)=C2NC2=C1C=C(C)C(C)=C2 YPZRHBJKEMOYQH-UYBVJOGSSA-N 0.000 description 1
- 108090000698 Formate Dehydrogenases Proteins 0.000 description 1
- 108010018962 Glucosephosphate Dehydrogenase Proteins 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 101710198130 NADPH-cytochrome P450 reductase Proteins 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000204735 Pseudomonas nitroreducens Species 0.000 description 1
- 241000589781 Pseudomonas oleovorans Species 0.000 description 1
- 240000005384 Rhizopus oryzae Species 0.000 description 1
- 235000013752 Rhizopus oryzae Nutrition 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 241000306282 Umbelopsis isabellina Species 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- 230000002210 biocatalytic effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000006957 competitive inhibition Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 108010058646 cyclohexanone oxygenase Proteins 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 238000003411 electrode reaction Methods 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002211 flavins Chemical class 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 108010060537 putidaredoxin Proteins 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- VRPOXTPJQZGFNR-UHFFFAOYSA-N rhodium(2+) monohydride Chemical compound [RhH+2] VRPOXTPJQZGFNR-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/22—Preparation of oxygen-containing organic compounds containing a hydroxy group aromatic
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P1/00—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Secondary Cells (AREA)
- Electric Double-Layer Capacitors Or The Like (AREA)
- Apparatus Associated With Microorganisms And Enzymes (AREA)
- Hybrid Cells (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10024314A DE10024314A1 (de) | 2000-05-17 | 2000-05-17 | Verfahren, umfassend die indirekte elektrochemische Regeneration von NAD(P)H |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200210128B true ZA200210128B (en) | 2004-03-10 |
Family
ID=7642483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200210128A ZA200210128B (en) | 2000-05-17 | 2002-12-13 | Method comprising the indirect electrochemical regeneration of NAD(P)H. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6991926B2 (ko) |
| EP (1) | EP1285082B1 (ko) |
| JP (1) | JP2003533208A (ko) |
| KR (1) | KR100812442B1 (ko) |
| CN (1) | CN100457915C (ko) |
| AT (1) | ATE349543T1 (ko) |
| AU (2) | AU5635701A (ko) |
| CA (1) | CA2409339A1 (ko) |
| DE (2) | DE10024314A1 (ko) |
| EE (1) | EE05114B1 (ko) |
| IL (2) | IL152298A0 (ko) |
| NO (1) | NO20025503L (ko) |
| NZ (1) | NZ522223A (ko) |
| RU (1) | RU2324739C2 (ko) |
| UA (1) | UA75074C2 (ko) |
| WO (1) | WO2001088172A1 (ko) |
| ZA (1) | ZA200210128B (ko) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1375671A1 (en) * | 2002-06-28 | 2004-01-02 | Eidgenössische Technische Hochschule Zürich | Selective functionalization of hydrocarbons with isolated oxygenases and mediator-based regeneration |
| EP2105500A1 (de) | 2008-03-26 | 2009-09-30 | Pharmazell GmbH | Neue 12alpha-Hydroxysteroiddehydrogenasen, deren Herstellung und deren Verwendung |
| US20100209968A1 (en) * | 2007-05-04 | 2010-08-19 | Akermin, Inc. | Immobilized enzymes and uses thereof |
| US20100003710A1 (en) | 2007-10-17 | 2010-01-07 | Ohmx Corporation | Electrochemical Assay for the Detection of Enzymes |
| KR101039753B1 (ko) | 2008-07-24 | 2011-06-09 | 한국과학기술원 | 금속 나노입자를 이용한 옥시도리덕타제 보조인자의전기화학적 재생방법 |
| EP2642291B1 (en) | 2009-08-07 | 2015-10-07 | Ohmx Corporation | Enzyme triggered redox altering chemical elimination (E-trace) immunoassay |
| WO2012012537A1 (en) | 2010-07-20 | 2012-01-26 | Ohmx Corporation | Novel chemistry used in biosensors |
| EP2441771A1 (de) | 2010-10-13 | 2012-04-18 | PharmaZell GmbH | Neue 12alpha-Hydroxysteroid- dehydrogenase-Mutanten, deren Herstellung deren Verwendung |
| WO2012100078A1 (en) | 2011-01-19 | 2012-07-26 | Ohmx Corporation | Enzyme triggered redox altering chemical elimination (e-trace) immmunoassay |
| CA2851632A1 (en) | 2011-10-17 | 2013-04-25 | Ohmx Corporation | Single, direct detection of hemoglobin a1c percentage using enzyme triggered redox altering chemical elimination (e-trace) immunoassay |
| WO2013067349A1 (en) | 2011-11-04 | 2013-05-10 | Ohmx Corporation | Novel chemistry used in biosensors |
| EP2802669A1 (en) | 2012-01-09 | 2014-11-19 | Ohmx Corporation | Enzyme cascade methods for e-trace assay signal amplification |
| EP2877851A1 (en) | 2012-07-27 | 2015-06-03 | Ohmx Corporation | Electric measurement of monolayers following pro-cleave detection of presence and activity of enzymes and other target analytes |
| WO2014018886A1 (en) | 2012-07-27 | 2014-01-30 | Ohmx Corporation | Electronic measurements of monolayers following homogeneous reactions of their components |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3221339A1 (de) * | 1982-06-05 | 1983-12-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zur elektrochemischen hydrierung von nicotinamidadenin-dinucleotid |
| DE3226888A1 (de) * | 1982-07-17 | 1984-01-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur durchfuehrung elektromikrobieller reduktionen |
| US5520786A (en) * | 1995-06-06 | 1996-05-28 | Bayer Corporation | Mediators suitable for the electrochemical regeneration of NADH, NADPH or analogs thereof |
| US6126795A (en) * | 1996-11-27 | 2000-10-03 | The United States Of America As Represented By The Secretary Of Commerce | Electroenzymatic reactor and method for enzymatic catalysis |
| US6599722B2 (en) * | 1998-12-22 | 2003-07-29 | Genencor International, Inc. | Method for producing ascorbic acid intermediates |
-
2000
- 2000-05-17 DE DE10024314A patent/DE10024314A1/de not_active Withdrawn
-
2001
- 2001-05-16 CN CNB018095283A patent/CN100457915C/zh not_active Expired - Fee Related
- 2001-05-16 UA UA20021210153A patent/UA75074C2/uk unknown
- 2001-05-16 US US10/276,227 patent/US6991926B2/en not_active Expired - Fee Related
- 2001-05-16 AU AU5635701A patent/AU5635701A/xx active Pending
- 2001-05-16 WO PCT/EP2001/005601 patent/WO2001088172A1/de active IP Right Grant
- 2001-05-16 RU RU2002134073/13A patent/RU2324739C2/ru not_active IP Right Cessation
- 2001-05-16 NZ NZ522223A patent/NZ522223A/en unknown
- 2001-05-16 CA CA002409339A patent/CA2409339A1/en not_active Abandoned
- 2001-05-16 EE EEP200200646A patent/EE05114B1/xx not_active IP Right Cessation
- 2001-05-16 AT AT01929648T patent/ATE349543T1/de not_active IP Right Cessation
- 2001-05-16 EP EP01929648A patent/EP1285082B1/de not_active Expired - Lifetime
- 2001-05-16 AU AU2001256357A patent/AU2001256357B2/en not_active Ceased
- 2001-05-16 KR KR1020027015095A patent/KR100812442B1/ko not_active IP Right Cessation
- 2001-05-16 IL IL15229801A patent/IL152298A0/xx unknown
- 2001-05-16 JP JP2001584554A patent/JP2003533208A/ja not_active Withdrawn
- 2001-05-16 DE DE50111739T patent/DE50111739D1/de not_active Expired - Fee Related
-
2002
- 2002-10-15 IL IL152298A patent/IL152298A/en not_active IP Right Cessation
- 2002-11-15 NO NO20025503A patent/NO20025503L/no not_active Application Discontinuation
- 2002-12-13 ZA ZA200210128A patent/ZA200210128B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO20025503D0 (no) | 2002-11-15 |
| US20030162270A1 (en) | 2003-08-28 |
| DE10024314A1 (de) | 2001-11-22 |
| CA2409339A1 (en) | 2002-11-15 |
| JP2003533208A (ja) | 2003-11-11 |
| US6991926B2 (en) | 2006-01-31 |
| WO2001088172A1 (de) | 2001-11-22 |
| DE50111739D1 (de) | 2007-02-08 |
| UA75074C2 (en) | 2006-03-15 |
| EP1285082B1 (de) | 2006-12-27 |
| KR100812442B1 (ko) | 2008-03-10 |
| NO20025503L (no) | 2002-11-15 |
| CN1429274A (zh) | 2003-07-09 |
| CN100457915C (zh) | 2009-02-04 |
| EP1285082A1 (de) | 2003-02-26 |
| AU5635701A (en) | 2001-11-26 |
| IL152298A0 (en) | 2003-05-29 |
| EE200200646A (et) | 2004-06-15 |
| ATE349543T1 (de) | 2007-01-15 |
| EE05114B1 (et) | 2008-12-15 |
| IL152298A (en) | 2009-09-01 |
| RU2002134073A (ru) | 2004-03-27 |
| NZ522223A (en) | 2006-02-24 |
| RU2324739C2 (ru) | 2008-05-20 |
| AU2001256357B2 (en) | 2006-09-28 |
| KR20030032951A (ko) | 2003-04-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Weckbecker et al. | Regeneration of nicotinamide coenzymes: principles and applications for the synthesis of chiral compounds | |
| Van Der Donk et al. | Recent developments in pyridine nucleotide regeneration | |
| Kohlmann et al. | Electroenzymatic synthesis | |
| Goldberg et al. | Biocatalytic ketone reduction—a powerful tool for the production of chiral alcohols—part I: processes with isolated enzymes | |
| Rodriguez et al. | Recent advances in cofactor regeneration systems applied to biocatalyzed oxidative processes | |
| US6991926B2 (en) | Method comprising the indirect electrochemical regeneration of NAD(P)H | |
| Schmitz et al. | Enzyme-based electrobiotechnological synthesis | |
| Adam et al. | Quantitative transformation of racemic 2-hydroxy acids into (R)-2-hydroxy acids by enantioselective oxidation with glycolate oxidase and subsequent reduction of 2-keto acids with D-lactate dehydrogenase | |
| Jia et al. | Myoglobin-catalyzed efficient in situ regeneration of NAD (P)+ and their synthetic biomimetic for dehydrogenase-mediated oxidations | |
| Knaus et al. | Ene‐reductases and their Applications | |
| US20210171995A1 (en) | Method for Using Electrochemical Bioreactor Module with Recovery of Cofactor | |
| Vilker et al. | Challenges in capturing oxygenase activity in vitro | |
| CN111471736A (zh) | 制备c1,2-位脱氢甾体化合物的方法 | |
| Ferrandi et al. | New trends in the in situ enzymatic recycling of NAD (P)(H) cofactors | |
| US7364884B2 (en) | Method for producing a hydroxylation catalyst and the use thereof | |
| Zhang et al. | Functional Electrodes for Enzymatic Electrosynthesis | |
| Höfler et al. | Photocatalysis to promote cell-free biocatalytic reactions | |
| Ng | Metabolism of non-growing cells and their application in biotransformation | |
| AU2005245554A1 (en) | Process for an enzymatic oxygenation by direct electrochemical regeneration of the FAD-dependant monooxygenase | |
| Burton et al. | Oxidizing Enzymes in Multi‐Step Biotransformation Processes | |
| GB2033428A (en) | Enzymatic Processes | |
| FR3097234A1 (fr) | Procede selectif de preparation de sulfoxydes par catalyse enzymatique | |
| FR3097233A1 (fr) | Procede selectif de preparation de sulfones par catalyse enzymatique | |
| Kataoka et al. | Screening of novel microbial enzymes and their application to chiral compound production | |
| Taj et al. | Biocatalytic Reduction of Aromatic Ketones Using Coenzyme Regeneration in An Electrochemical Process |