UA75074C2 - Method for the electroenzymatic production of 2,3-dihydroxyphenyl derivatives and method foe electrochemical regeneration of nad(p)h from nad(p)+ - Google Patents
Method for the electroenzymatic production of 2,3-dihydroxyphenyl derivatives and method foe electrochemical regeneration of nad(p)h from nad(p)+ Download PDFInfo
- Publication number
- UA75074C2 UA75074C2 UA20021210153A UA20021210153A UA75074C2 UA 75074 C2 UA75074 C2 UA 75074C2 UA 20021210153 A UA20021210153 A UA 20021210153A UA 20021210153 A UA20021210153 A UA 20021210153A UA 75074 C2 UA75074 C2 UA 75074C2
- Authority
- UA
- Ukraine
- Prior art keywords
- concentration
- rhodium
- mas
- hydride
- oxidation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 56
- 230000008929 regeneration Effects 0.000 title claims abstract description 38
- 238000011069 regeneration method Methods 0.000 title claims abstract description 38
- -1 2,3-dihydroxyphenyl Chemical class 0.000 title claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 42
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 41
- 239000001301 oxygen Substances 0.000 claims abstract description 41
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- 239000000758 substrate Substances 0.000 claims abstract description 30
- 230000002829 reductive effect Effects 0.000 claims abstract description 23
- 108010074633 Mixed Function Oxygenases Proteins 0.000 claims abstract description 22
- 102000008109 Mixed Function Oxygenases Human genes 0.000 claims abstract description 22
- 230000002255 enzymatic effect Effects 0.000 claims abstract description 19
- 108010053948 2-hydroxybiphenyl 3-monooxygenase Proteins 0.000 claims abstract description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 28
- 230000003647 oxidation Effects 0.000 claims description 23
- 230000015572 biosynthetic process Effects 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 21
- 229910052703 rhodium Inorganic materials 0.000 claims description 16
- 239000010948 rhodium Substances 0.000 claims description 16
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 15
- 230000001590 oxidative effect Effects 0.000 claims description 12
- 230000009467 reduction Effects 0.000 claims description 10
- 230000009466 transformation Effects 0.000 claims description 10
- 230000003993 interaction Effects 0.000 claims description 9
- 102000016938 Catalase Human genes 0.000 claims description 8
- 108010053835 Catalase Proteins 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- SETMGIIITGNLAS-UHFFFAOYSA-N spizofurone Chemical compound O=C1C2=CC(C(=O)C)=CC=C2OC21CC2 SETMGIIITGNLAS-UHFFFAOYSA-N 0.000 claims description 8
- 229950001870 spizofurone Drugs 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 238000005805 hydroxylation reaction Methods 0.000 claims description 6
- 229910021607 Silver chloride Inorganic materials 0.000 claims description 5
- 230000001419 dependent effect Effects 0.000 claims description 5
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 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
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 230000033444 hydroxylation Effects 0.000 claims description 4
- 125000002097 pentamethylcyclopentadienyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 238000006735 epoxidation reaction Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002560 nitrile group Chemical group 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 150000003283 rhodium Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 239000011669 selenium Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- BAWFJGJZGIEFAR-NNYOXOHSSA-O NAD(+) 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-O 0.000 abstract 2
- 102000004190 Enzymes Human genes 0.000 description 24
- 108090000790 Enzymes Proteins 0.000 description 24
- 230000008569 process Effects 0.000 description 15
- 230000000694 effects Effects 0.000 description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- 239000000872 buffer Substances 0.000 description 9
- 238000006722 reduction reaction Methods 0.000 description 9
- 230000001404 mediated effect Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 6
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 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
- 230000005587 bubbling Effects 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- YKOQAAJBYBTSBS-UHFFFAOYSA-N biphenyl-2,3-diol Chemical group OC1=CC=CC(C=2C=CC=CC=2)=C1O YKOQAAJBYBTSBS-UHFFFAOYSA-N 0.000 description 4
- 229910001882 dioxygen Inorganic materials 0.000 description 4
- 230000000737 periodic effect Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012431 aqueous reaction media Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 238000006911 enzymatic reaction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 235000010292 orthophenyl phenol Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 101710163168 Flavin-dependent monooxygenase Proteins 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol 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
- 239000004280 Sodium formate Substances 0.000 description 2
- 101710091169 Thiol-specific monooxygenase Proteins 0.000 description 2
- 238000010521 absorption reaction Methods 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
- 230000002210 biocatalytic effect Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000006213 oxygenation reaction Methods 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000006479 redox reaction Methods 0.000 description 2
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 2
- 235000019254 sodium formate Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical class 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
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 1
- 108090000698 Formate Dehydrogenases Proteins 0.000 description 1
- 108010018962 Glucosephosphate Dehydrogenase Proteins 0.000 description 1
- 101710198130 NADPH-cytochrome P450 reductase Proteins 0.000 description 1
- 241000256856 Vespidae Species 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000004074 biphenyls Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 235000019994 cava Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000006957 competitive inhibition Effects 0.000 description 1
- 108010058646 cyclohexanone oxygenase Proteins 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
- 230000009977 dual effect Effects 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 238000010828 elution Methods 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
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- VWWQXMAJTJZDQX-UYBVJOGSSA-N flavin adenine dinucleotide Chemical compound C1=NC2=C(N)N=CN=C2N1[C@@H]([C@H](O)[C@@H]1O)O[C@@H]1CO[P@](O)(=O)O[P@@](O)(=O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C2=NC(=O)NC(=O)C2=NC2=C1C=C(C)C(C)=C2 VWWQXMAJTJZDQX-UYBVJOGSSA-N 0.000 description 1
- 235000019162 flavin adenine dinucleotide Nutrition 0.000 description 1
- 239000011714 flavin adenine dinucleotide Substances 0.000 description 1
- 229940093632 flavin-adenine dinucleotide Drugs 0.000 description 1
- 150000002211 flavins Chemical class 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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229960002899 hydroxyprogesterone Drugs 0.000 description 1
- 208000033065 inborn errors of immunity Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 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
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 238000005191 phase separation 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
- 238000011084 recovery Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 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
- 238000000844 transformation Methods 0.000 description 1
- CZPRKINNVBONSF-UHFFFAOYSA-M zinc;dioxido(oxo)phosphanium Chemical compound [Zn+2].[O-][P+]([O-])=O CZPRKINNVBONSF-UHFFFAOYSA-M 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 (2)
| 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 |
| PCT/EP2001/005601 WO2001088172A1 (de) | 2000-05-17 | 2001-05-16 | Verfahren, umfassend die indirekte elektrochemische regeneration von nad(p)h |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA75074C2 true UA75074C2 (en) | 2006-03-15 |
Family
ID=7642483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20021210153A UA75074C2 (en) | 2000-05-17 | 2001-05-16 | Method for the electroenzymatic production of 2,3-dihydroxyphenyl derivatives and method foe electrochemical regeneration of nad(p)h from nad(p)+ |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6991926B2 (no) |
| EP (1) | EP1285082B1 (no) |
| JP (1) | JP2003533208A (no) |
| KR (1) | KR100812442B1 (no) |
| CN (1) | CN100457915C (no) |
| AT (1) | ATE349543T1 (no) |
| AU (2) | AU2001256357B2 (no) |
| CA (1) | CA2409339A1 (no) |
| DE (2) | DE10024314A1 (no) |
| EE (1) | EE05114B1 (no) |
| IL (2) | IL152298A0 (no) |
| NO (1) | NO20025503D0 (no) |
| NZ (1) | NZ522223A (no) |
| RU (1) | RU2324739C2 (no) |
| UA (1) | UA75074C2 (no) |
| WO (1) | WO2001088172A1 (no) |
| ZA (1) | ZA200210128B (no) |
Families Citing this family (15)
| 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 |
| CA2686161A1 (en) * | 2007-05-04 | 2008-11-13 | Akermin, Inc. | Immobilized enzymes and uses thereof |
| EP2210268A4 (en) * | 2007-10-17 | 2012-02-15 | Ohmx Corp | IN THE BIOSENSORS USED NEW CHEMISTRY |
| US8951400B2 (en) | 2007-10-17 | 2015-02-10 | Ohmx Corporation | Chemistry used in biosensors |
| KR101039753B1 (ko) | 2008-07-24 | 2011-06-09 | 한국과학기술원 | 금속 나노입자를 이용한 옥시도리덕타제 보조인자의전기화학적 재생방법 |
| CA2770071C (en) | 2009-08-07 | 2014-07-15 | Ohmx Corporation | Enzyme triggered redox altering chemical elimination (e-trace) immunoassay |
| US9250234B2 (en) | 2011-01-19 | 2016-02-02 | Ohmx Corporation | Enzyme triggered redox altering chemical elimination (E-TRACE) immunoassay |
| EP2441771A1 (de) | 2010-10-13 | 2012-04-18 | PharmaZell GmbH | Neue 12alpha-Hydroxysteroid- dehydrogenase-Mutanten, deren Herstellung deren Verwendung |
| WO2013059293A1 (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 |
| EP2773650A1 (en) | 2011-11-04 | 2014-09-10 | Ohmx Corporation | Novel chemistry used in biosensors |
| US9250203B2 (en) | 2012-01-09 | 2016-02-02 | Ohmx Corporation | Enzyme cascade methods for E-TRACE assay signal amplification |
| US9416390B2 (en) | 2012-07-27 | 2016-08-16 | Ohmx Corporation | Electric measurement of monolayers following pro-cleave detection of presence and activity of enzymes and other target analytes |
| EP2877592B1 (en) | 2012-07-27 | 2016-09-21 | Ohmx Corporation | Electronic measurements of monolayers following homogeneous reactions of their components |
| WO2020262136A1 (ja) * | 2019-06-26 | 2020-12-30 | 国立研究開発法人産業技術総合研究所 | メタン生成補酵素を用いた電気化学的バイオガス生産システム |
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 JP JP2001584554A patent/JP2003533208A/ja not_active Withdrawn
- 2001-05-16 CN CNB018095283A patent/CN100457915C/zh not_active Expired - Fee Related
- 2001-05-16 EE EEP200200646A patent/EE05114B1/xx not_active IP Right Cessation
- 2001-05-16 RU RU2002134073/13A patent/RU2324739C2/ru not_active IP Right Cessation
- 2001-05-16 US US10/276,227 patent/US6991926B2/en not_active Expired - Fee Related
- 2001-05-16 IL IL15229801A patent/IL152298A0/xx unknown
- 2001-05-16 AU AU2001256357A patent/AU2001256357B2/en not_active Ceased
- 2001-05-16 NZ NZ522223A patent/NZ522223A/en unknown
- 2001-05-16 EP EP01929648A patent/EP1285082B1/de not_active Expired - Lifetime
- 2001-05-16 AT AT01929648T patent/ATE349543T1/de not_active IP Right Cessation
- 2001-05-16 KR KR1020027015095A patent/KR100812442B1/ko not_active IP Right Cessation
- 2001-05-16 AU AU5635701A patent/AU5635701A/xx active Pending
- 2001-05-16 CA CA002409339A patent/CA2409339A1/en not_active Abandoned
- 2001-05-16 WO PCT/EP2001/005601 patent/WO2001088172A1/de active IP Right Grant
- 2001-05-16 UA UA20021210153A patent/UA75074C2/uk unknown
- 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/NO20025503D0/no not_active Application Discontinuation
- 2002-12-13 ZA ZA200210128A patent/ZA200210128B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE349543T1 (de) | 2007-01-15 |
| IL152298A0 (en) | 2003-05-29 |
| WO2001088172A1 (de) | 2001-11-22 |
| EP1285082A1 (de) | 2003-02-26 |
| EE200200646A (et) | 2004-06-15 |
| CN1429274A (zh) | 2003-07-09 |
| RU2002134073A (ru) | 2004-03-27 |
| US20030162270A1 (en) | 2003-08-28 |
| NO20025503L (no) | 2002-11-15 |
| DE50111739D1 (de) | 2007-02-08 |
| IL152298A (en) | 2009-09-01 |
| JP2003533208A (ja) | 2003-11-11 |
| RU2324739C2 (ru) | 2008-05-20 |
| AU5635701A (en) | 2001-11-26 |
| NZ522223A (en) | 2006-02-24 |
| KR100812442B1 (ko) | 2008-03-10 |
| NO20025503D0 (no) | 2002-11-15 |
| KR20030032951A (ko) | 2003-04-26 |
| DE10024314A1 (de) | 2001-11-22 |
| US6991926B2 (en) | 2006-01-31 |
| CA2409339A1 (en) | 2002-11-15 |
| CN100457915C (zh) | 2009-02-04 |
| EP1285082B1 (de) | 2006-12-27 |
| AU2001256357B2 (en) | 2006-09-28 |
| EE05114B1 (et) | 2008-12-15 |
| ZA200210128B (en) | 2004-03-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Lee et al. | Enzyme-catalyzed organic synthesis: a comparison of strategies for in situ regeneration of NAD from NADH | |
| UA75074C2 (en) | Method for the electroenzymatic production of 2,3-dihydroxyphenyl derivatives and method foe electrochemical regeneration of nad(p)h from nad(p)+ | |
| Van Der Donk et al. | Recent developments in pyridine nucleotide regeneration | |
| De Wildeman et al. | Biocatalytic reductions: from lab curiosity to “first choice” | |
| Rodriguez et al. | Recent advances in cofactor regeneration systems applied to biocatalyzed oxidative processes | |
| Zhang et al. | Nonconventional regeneration of redox enzymes–a practical approach for organic synthesis? | |
| Sharma et al. | Redox biocatalysis: quantitative comparisons of nicotinamide cofactor regeneration methods | |
| US20210171995A1 (en) | Method for Using Electrochemical Bioreactor Module with Recovery of Cofactor | |
| Schmitz et al. | Enzyme-based electrobiotechnological synthesis | |
| Schulz et al. | Electromicrobial regeneration of pyridine nucleotides and other preparative redox transformations with Clostridium thermoaceticum | |
| US4749670A (en) | Selective regeneration of mediators in the presence of a catalyst and surfactant | |
| Hilt et al. | Efficient In‐Situ Redox Catalytic NAD (P)+ Regeneration in Enzymatic Synthesis Using Transition‐Metal Complexes of 1, 10‐Phenanthroline‐5, 6‐dione and Its N‐Monomethylated Derivative as Catalysts | |
| US6365380B2 (en) | Method for stereoselectively inverting a chiral center of a chemical compound using an enzyme and a metal catalyst | |
| Lin et al. | Biocatalytic epoxidation for green synthesis | |
| CN111217744A (zh) | 一种d-氨基酸基nad+类似物及其合成和应用 | |
| EP0099742A1 (en) | Enzymatic reaction process | |
| US5192687A (en) | Electroenzymatic method for producing compounds of controlled enantiomeric purity | |
| Röllig et al. | Hybrid catalysis for enantioselective Baeyer–Villiger oxidation and stereoselective epoxidation: a Cp* Ir complex to fuel FMN and FAD reduction for flavoprotein monooxygenase modules | |
| Wu | Hui Lin1, Meng-Yu Xu1, 2, Yan Liu1, 2, and | |
| Wei et al. | Bio‐electrocatalytic Alkene Reduction Using Ene‐Reductases with Methyl Viologen as Electron Mediator | |
| Panke | Production of (S)-styrene oxide with recombinant bacteria | |
| Toogood et al. | Biocatalyst identification by anaerobic high-throughput screening of enzyme libraries and anaerobic microorganisms | |
| Fernández‐Álvaro et al. | Reductases: From Natural Diversity to Established Biocatalysis and to Emerging Enzymatic Activities | |
| Tramper¹ et al. | SECOND-GENERATION BIOCATALYSIS | |
| Hammerich et al. | NAD+ XPD-Mediatorred. |