HRP20191514T1 - Postupak enzimske regeneracije redoks kofaktora - Google Patents
Postupak enzimske regeneracije redoks kofaktora Download PDFInfo
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- HRP20191514T1 HRP20191514T1 HRP20191514T HRP20191514T1 HR P20191514 T1 HRP20191514 T1 HR P20191514T1 HR P20191514 T HRP20191514 T HR P20191514T HR P20191514 T1 HRP20191514 T1 HR P20191514T1
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- oxidation
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- 238000000034 method Methods 0.000 title claims 13
- 230000008929 regeneration Effects 0.000 title claims 7
- 238000011069 regeneration method Methods 0.000 title claims 7
- 230000002255 enzymatic effect Effects 0.000 title claims 6
- 238000006243 chemical reaction Methods 0.000 claims 12
- 238000007254 oxidation reaction Methods 0.000 claims 12
- 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 claims 11
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 238000006722 reduction reaction Methods 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 230000003647 oxidation Effects 0.000 claims 7
- 125000004043 oxo group Chemical group O=* 0.000 claims 7
- MIHNUBCEFJLAGN-RAEYQWLJSA-N 3alpha,7beta-dihydroxy-12-oxo-5beta-cholanic acid Chemical compound C([C@H]1C[C@@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)C(=O)C1 MIHNUBCEFJLAGN-RAEYQWLJSA-N 0.000 claims 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 6
- 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 5
- RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 claims 4
- 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 claims 4
- 150000002440 hydroxy compounds Chemical class 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- 108010062875 Hydroxysteroid Dehydrogenases Proteins 0.000 claims 3
- 102000011145 Hydroxysteroid Dehydrogenases Human genes 0.000 claims 3
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims 3
- 230000000707 stereoselective effect Effects 0.000 claims 3
- 239000000758 substrate Substances 0.000 claims 3
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 claims 2
- RHCPKKNRWFXMAT-RRWYKFPJSA-N 3alpha,12alpha-dihydroxy-7-oxo-5beta-cholanic acid Chemical compound C1C[C@@H](O)C[C@H]2CC(=O)[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(O)=O)C)[C@@]4(C)[C@@H](O)C[C@@H]3[C@]21C RHCPKKNRWFXMAT-RRWYKFPJSA-N 0.000 claims 2
- 108010021809 Alcohol dehydrogenase Proteins 0.000 claims 2
- 102000007698 Alcohol dehydrogenase Human genes 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 102000003855 L-lactate dehydrogenase Human genes 0.000 claims 2
- 108700023483 L-lactate dehydrogenases Proteins 0.000 claims 2
- 108010026217 Malate Dehydrogenase Proteins 0.000 claims 2
- 102000013460 Malate Dehydrogenase Human genes 0.000 claims 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 claims 2
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 claims 2
- 238000006345 epimerization reaction Methods 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 238000006317 isomerization reaction Methods 0.000 claims 2
- 229940049920 malate Drugs 0.000 claims 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 2
- RUDATBOHQWOJDD-UZVSRGJWSA-N ursodeoxycholic acid Chemical compound C([C@H]1C[C@@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-UZVSRGJWSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 102100039358 3-hydroxyacyl-CoA dehydrogenase type-2 Human genes 0.000 claims 1
- MIHNUBCEFJLAGN-DMMBONCOSA-N 3alpha,7alpha-dihydroxy-12-oxo-5beta-cholanic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)C(=O)C1 MIHNUBCEFJLAGN-DMMBONCOSA-N 0.000 claims 1
- 108010032887 7 beta-hydroxysteroid dehydrogenase Proteins 0.000 claims 1
- 108010014831 7-alpha-hydroxysteroid dehydrogenase Proteins 0.000 claims 1
- 239000004380 Cholic acid Substances 0.000 claims 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims 1
- 241000588724 Escherichia coli Species 0.000 claims 1
- 229930091371 Fructose Natural products 0.000 claims 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims 1
- 239000005715 Fructose Substances 0.000 claims 1
- 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 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 1
- 108010007843 NADH oxidase Proteins 0.000 claims 1
- 241001464870 [Ruminococcus] torques Species 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 1
- 229960001091 chenodeoxycholic acid Drugs 0.000 claims 1
- 229960002471 cholic acid Drugs 0.000 claims 1
- 235000019416 cholic acid Nutrition 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 claims 1
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000006479 redox reaction Methods 0.000 claims 1
- 239000000600 sorbitol Substances 0.000 claims 1
- 229960003604 testosterone Drugs 0.000 claims 1
- BHQCQFFYRZLCQQ-UTLSPDKDSA-N ursocholic acid Chemical compound C([C@H]1C[C@@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-UTLSPDKDSA-N 0.000 claims 1
- 229960001661 ursodiol Drugs 0.000 claims 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/02—Monosaccharides
-
- 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/26—Preparation of nitrogen-containing carbohydrates
- C12P19/28—N-glycosides
- C12P19/30—Nucleotides
- C12P19/36—Dinucleotides, e.g. nicotineamide-adenine dinucleotide phosphate
-
- 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
- C12P33/00—Preparation of steroids
-
- 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
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/002—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by oxidation/reduction reactions
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Genetics & Genomics (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Molecular Biology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
Claims (12)
1. Proces enzimske regeneracije redoks kofaktora NAD+ / NADH i NADP+ / NADPH u reakciji s jednim reaktorom (one-pot reaction), pri čemu, kao rezultat najmanje dvije daljnje enzimski katalizirane redoks reakcije koje se odvijaju u istoj reakcijskoj šarži (reakcije koje stvaraju proizvod), redoks kofaktor NAD+ / NADH se akumulira u reduciranom obliku kao NADH, a redoks kofaktor NADP+ / NADPH se akumulira u svom oksidiranom obliku kao NADP+, naznačen time, da:
a) u regeneracijskoj reakciji koja pretvara NADH u NAD+, kisik se reducira pomoću NADH oksidaze ili piruvat pomoću laktatne dehidrogenaze i
b) u regeneracijskoj reakciji koja NADP+ pretvara u NADPH, 2-propanol se oksidira pomoću alkohol-dehidrogenaze ili malata pomoću malat dehidrogenaze.
2. Postupak u skladu s patentnim zahtjevom 1, naznačen time, da se reakcija(e) oksidacije i reakcija(e) redukcije odvijaju na istom supstratu (molekularna okosnica).
3. Postupak u skladu s patentnim zahtjevom 1 ili 2, naznačen time, da se reakcija(e) oksidacije i reakcija(e) redukcije odvijaju kronološki paralelno.
4. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time, da se u reakciji regeneracije koja NADP+ pretvara u NADPH, 2-propanol oksidira u aceton pomoću alkohol dehidrogenaze.
5. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time, da se u reakciji regeneracije koja NADH pretvara u NAD+, piruvat reducira u laktat pomoću laktatne dehidrogenaze.
6. Postupak u skladu s patentnim zahtjevom 5, naznačen time, da se u reakciji regeneracije koja NADP+ pretvara u NADPH, malat oksidira u piruvat i CO2 pomoću malat dehidrogenaze.
7. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 5, naznačen time, da se upotrebljava za provođenje barem jedne reakcije oksidacije i barem jedne reakcije redukcije, u istoj reakcijskoj šarži na spojevima opće formule
pri čemu
R4 označava vodik, metilnu skupinu, hidroksi skupinu ili okso skupinu,
R5 označava vodik, hidroksi skupinu, okso skupinu ili metilnu skupinu,
R6 označava vodik ili hidroksi skupinu,
R7 označava vodik, -COR13, pri čemu je R13 C1-C4 alkilna skupina koja je nesupstituirana ili je supstituirana s hidroksi skupinom, ili C1-C4 karboksi alkilna skupina koja je supstituirana, osobito s hidroksi skupinom, ili nesupstituirana, ili R6 i R7 zajedno označavaju okso grupu,
R8 označava vodik, metilnu skupinu, hidroksi skupinu ili okso skupinu,
R9 označava vodik, metilnu skupinu, hidroksi skupinu ili okso skupinu,
R10 označava vodik, metilnu skupinu ili halogen,
R11 označava vodik, metilnu skupinu, hidroksi skupinu, okso skupinu ili halogen, a
R12 označava vodik, hidroksi skupinu, okso skupinu ili metilnu skupinu, pri čemu strukturni element
označava benzenski prsten ili prsten koji sadržava 6 atoma ugljika i 0, 1 ili 2 C-C dvostruke veze; osobito pri čemu su supstrat(i) osigurani u koncentraciji <5% (w / v) u reakcijskoj šarži za reakciju(e) redukcije koja sudjeluje u stvaranju produkta.
8. Postupak u skladu s patentnim zahtjevom 7, naznačen time, da se upotrebljava za pretvorbu dehidroepiandrosterona (DHEA) formule
u testosteron formule
9. Postupak u skladu s patentnim zahtjevom 7, naznačen time, da se koristi za enzimsku epimerizaciju 3α,7α-dihidroksi-5β-kolanske kiseline (kenodeoksikolične kiseline) formule
u ketolitokoličnu kiselinu formule
oksidacijom,
i u stereoizomerni hidroksi spoj 3α,7β -dihidroksi-5β-kolanske kiseline (ursodeoksikolična kiselina) formule
naknadnom redukcijom,
upotrebom dviju suprotnih stereospecifičnih hidroksisteroidnih dehidrogenaza, pri čemu, po izboru, oksidacijsku reakciju katalizira 7α-hidroksisteroid dehidrogenaza iz E. coli, i / ili reakciju redukcije katalizira 7β-hidroksisteroid dehidrogenaza iz Ruminococcus torques.
10. Postupak u skladu s patentnim zahtjevom 7, naznačen time, da se koristi za enzimsku epimerizaciju 3α,7α,12α-trihidroksi-5β-kolanske kiseline (količna kiselina) formule
bilo
A) putem oksidacije, čime se dobije 3α,7α-dihidroksi-12-okso-5β-kolanska kiselina (12-okso-CDC) formule
koja dalje reagira da se dobije 3α-hidroksi-7,12-diokso-5β-kolanska kiselina (12okso-KLC ) formule
i kasnije reducira na stereoizomerni hidroksi spoj 3α,7β -dihidroksi-12-okso-5β- kolanska kiselina (12-keto-ursodeoksikolična kiselina) formule
ili
B) oksidacijom da bi se dobio 3α,12α-dihidroksi-7-okso-5β-kolanska kiselina formule
praćena enzimskom oksidacijom radi dobivanja 3α-hidroksi-7,12-diokso-5β- kolanske kiseline (12okso-KLC) formule
i kasnije reduciranje da se dobije stereoizomerna hidroksi spoj 3α,7β -dihidroksi- 12-okso-5β-kolanska kiselina (12-keto-ursodeoksikolična kiselina) formule XII ili
C) oksidacijom da bi se dobio 3α,12α -dihidroksi-7-okso- 5β-kolanska kiselina formule XIII, a potom enzimska redukcija da se dobije 3α,7β,12α-triidroksi-5β- kolanske kiseline formule
i naknadna oksidacija da se dobije stereoizomerni hidroksi spoj 3α,7β-dihidroksi- 12-okso-5β-kolanske kiseline (12 -keto-ursodeoksikolična kiselina) formule XII;
upotrebom tri stereospecifične hidroksisteroidne dehidrogenaze; s dvije od tri stereospecifične hidroksisteroidne dehidrogenaze koje imaju suprotnu specifičnost.
11. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 6, naznačen time, da se upotrebljava za izomerizaciju C5- ili C6- šećera, osobito za izomerizaciju glukoze redukcijom u sorbitol i naknadnu oksidaciju u fruktozu.
12. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 11, naznačen time, da se supstrat(i) za oksidacijsku reakciju(e) koji sudjeluju u stvaranju produkta osiguravaju u reakcijskoj šarži u koncentraciji od 5% (w / v) i više, osobito 7% (w / v) i više, osobito 9% (w / v) i više.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12450007 | 2012-02-07 | ||
| PCT/EP2012/067781 WO2013117251A1 (de) | 2012-02-07 | 2012-09-12 | Verfahren zur enzymatischen regenerierung von redoxkofaktoren |
| AT12842012A AT513721B1 (de) | 2012-12-10 | 2012-12-10 | Verfahren zur enzymatischen Regenerierung von Redoxkofaktoren |
| PCT/EP2013/052313 WO2013117584A1 (de) | 2012-02-07 | 2013-02-06 | Verfahren zur enzymatischen regenerierung von redoxkofaktoren |
| EP13703568.9A EP2812439B1 (de) | 2012-02-07 | 2013-02-06 | Verfahren zur enzymatischen regenerierung von redoxkofaktoren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20191514T1 true HRP20191514T1 (hr) | 2019-11-29 |
Family
ID=48946925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20191514 HRP20191514T1 (hr) | 2012-02-07 | 2019-08-22 | Postupak enzimske regeneracije redoks kofaktora |
Country Status (29)
| Country | Link |
|---|---|
| US (3) | US9644227B2 (hr) |
| EP (1) | EP2812439B1 (hr) |
| JP (1) | JP6329086B2 (hr) |
| KR (1) | KR102022137B1 (hr) |
| CN (2) | CN113337568A (hr) |
| AR (1) | AR089841A1 (hr) |
| AU (1) | AU2013218042B2 (hr) |
| BR (1) | BR112014019287B1 (hr) |
| CA (1) | CA2862384C (hr) |
| ES (1) | ES2742381T3 (hr) |
| HK (1) | HK1204010A1 (hr) |
| HR (1) | HRP20191514T1 (hr) |
| HU (1) | HUE044690T2 (hr) |
| IN (1) | IN2014DN07015A (hr) |
| LT (1) | LT2812439T (hr) |
| MX (1) | MX358771B (hr) |
| MY (1) | MY172493A (hr) |
| NZ (1) | NZ627477A (hr) |
| PH (1) | PH12014501770B1 (hr) |
| PL (1) | PL2812439T3 (hr) |
| PT (1) | PT2812439T (hr) |
| RS (1) | RS59114B1 (hr) |
| RU (1) | RU2635087C2 (hr) |
| SA (1) | SA113340270B1 (hr) |
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| SI (1) | SI2812439T1 (hr) |
| TW (1) | TW201343623A (hr) |
| UA (1) | UA117453C2 (hr) |
| WO (1) | WO2013117584A1 (hr) |
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| TW201343623A (zh) | 2012-02-07 | 2013-11-01 | Annikki Gmbh | 使氧化還原輔因子經酶催化再生之方法 |
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| US10253340B2 (en) * | 2013-03-27 | 2019-04-09 | Annikki Gmbh | Method for the isomerisation of glucose |
| EP3636743A1 (en) * | 2014-04-02 | 2020-04-15 | The Regents of The University of California | A synthetic biochemistry molecular purge valve module that maintains co-factor balance |
| US9890397B1 (en) | 2015-07-15 | 2018-02-13 | Gaurab Chakrabarti | Hydrogen peroxide production method, system, and apparatus |
| CN114686532A (zh) * | 2015-07-24 | 2022-07-01 | 安尼基有限责任公司 | 用于酶促制备混合糖的氧化产物和还原产物的方法 |
| CN105861613B (zh) * | 2016-03-30 | 2019-12-13 | 中山百灵生物技术有限公司 | 一种熊去氧胆酸制备方法 |
| EP3464606A1 (de) | 2016-05-23 | 2019-04-10 | Annikki GmbH | Verfahren zur enzymatischen umwandlung von d-glucose in d-fructose via d-sorbitol |
| WO2018036982A1 (de) * | 2016-08-22 | 2018-03-01 | Pharmazell Gmbh | Chemisch-biokatalytisches verfahren zur herstellung von ursodesoxycholsäure |
| US11203769B1 (en) | 2017-02-13 | 2021-12-21 | Solugen, Inc. | Hydrogen peroxide and gluconic acid production |
| CN106957886A (zh) * | 2017-03-01 | 2017-07-18 | 南京远淑医药科技有限公司 | 一种熊去氧胆酸的制备方法 |
| CN107315038B (zh) * | 2017-07-06 | 2019-06-18 | 江南大学 | 一种批量化对酒类样品中氨基甲酸乙酯快速测定的方法 |
| JP6559745B2 (ja) | 2017-08-23 | 2019-08-14 | 株式会社東芝 | 半導体デバイス検査装置、半導体デバイス検査方法、そのプログラム、半導体装置およびその製造方法 |
| CN108251491A (zh) * | 2018-03-09 | 2018-07-06 | 中山百灵生物技术有限公司 | 一种酶促法合成熊去氧胆酸的方法 |
| US11530391B2 (en) | 2018-04-06 | 2022-12-20 | Braskem S.A. | NADH-dependent enzyme mutants to convert acetone into isopropanol |
| CN109055473A (zh) * | 2018-08-21 | 2018-12-21 | 湖南宝利士生物技术有限公司 | 一种基于酶法偶联技术合成熊去氧胆酸和高手性纯度d-氨基酸的方法 |
| 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 |
| CN109486896A (zh) * | 2018-12-04 | 2019-03-19 | 南京工业大学 | 一种催化拆分制备异甘草酸的方法 |
| CN109486895A (zh) * | 2018-12-04 | 2019-03-19 | 南京工业大学 | 一种催化拆分制备异甘草酸的方法 |
| CN110387360B (zh) * | 2019-06-18 | 2021-12-28 | 华东理工大学 | 羟基类固醇脱氢酶及其在合成熊去氧胆酸前体中的应用 |
| CN111593085A (zh) * | 2020-05-26 | 2020-08-28 | 四川澄华生物科技有限公司 | 一种12-酮基胆酸的制备方法 |
| CN112813128A (zh) * | 2021-01-12 | 2021-05-18 | 中山百灵生物技术股份有限公司 | 一种别熊去氧胆酸的合成方法 |
| KR102504343B1 (ko) | 2021-02-22 | 2023-02-28 | 전남대학교산학협력단 | 단량체 이소시트레이트 디하이드로게나아제에 기반한 nadph 재생 시스템 및 이의 용도 |
| CN116536279B (zh) * | 2022-01-25 | 2023-11-14 | 杭州馨海酶源生物科技有限公司 | 一种基因工程菌及在制备去氢表雄酮上的应用 |
| EP4464786A1 (de) | 2023-05-15 | 2024-11-20 | Annikki GmbH | Verfahren zur herstellung von wässerigen lösungen enthaltend d-psicose oder l-psicose |
| EP4446422A2 (de) | 2023-03-15 | 2024-10-16 | Annikki GmbH | Verfahren zur herstellung einer wässerigen lösung enthaltend l-psicose |
| WO2024189215A2 (de) | 2023-03-15 | 2024-09-19 | Annikki Gmbh | Verfahren zur herstellung einer wässerigen lösung enthaltend d-psicose |
| WO2024213621A2 (de) | 2023-04-11 | 2024-10-17 | Annikki Gmbh | Verfahren zur herstellung von allitol |
| EP4446421A1 (de) | 2023-04-11 | 2024-10-16 | Annikki GmbH | Verfahren zur herstellung von allitol |
| WO2024236043A1 (de) | 2023-05-15 | 2024-11-21 | Annikki Gmbh | Verfahren zur herstellung von d-talitol, d-tagatose und d-psicose |
| EP4464785A1 (de) | 2023-05-15 | 2024-11-20 | Annikki GmbH | Verfahren zur herstellung von d-talitol, d-tagatose und d-psicose |
| EP4488376A1 (de) | 2023-07-07 | 2025-01-08 | Annikki GmbH | Verfahren zur herstellung einer wässerigen lösung enthaltend l-sorbose |
| EP4488374A1 (de) | 2023-07-07 | 2025-01-08 | Annikki GmbH | Verfahren zur herstellung einer wässerigen lösung enthaltend ethylenglycol |
| EP4488368A1 (en) | 2023-07-07 | 2025-01-08 | Annikki GmbH | Nad(p)h oxidase |
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| HUP0105331A3 (en) | 1999-12-03 | 2005-10-28 | Kaneka Corp | Novel carbonyl reductase, gene thereof and method of using the same |
| DE10140088A1 (de) | 2001-08-16 | 2003-03-13 | Degussa | NADH-Oxidase aus Lactobacillus |
| AU2003257986A1 (en) | 2002-07-31 | 2004-02-16 | Georgia Tech Research Corporation | Methods and compositions for nad(p)(h) oxidases |
| DE10240603A1 (de) | 2002-09-03 | 2004-03-11 | Degussa Ag | Verwendung von Malat-Dehydrogenase zur NADH-Regenerierung |
| EP1731618A1 (en) | 2005-06-07 | 2006-12-13 | Prodotti Chimici E Alimentari Spa | Process for the selective oxydation of colic acid |
| AT503486B1 (de) * | 2006-04-11 | 2008-05-15 | Iep Gmbh | Verfahren zur enantioselektiven reduktion von steroiden |
| EP1925674A1 (en) | 2006-11-27 | 2008-05-28 | Universiteit van Amsterdam | Regeneration of NADPH and/or NADH cofactors |
| AT506639A1 (de) | 2008-04-01 | 2009-10-15 | Kroutil Wolfgang Dipl Ing Dr T | Verfahren zur deracemisierung von enantiomerengemischen unter verwendung von enzymsystemen |
| IT1398729B1 (it) | 2009-07-01 | 2013-03-18 | F S I Fabbrica Italiana Sint | Processo per la preparazione di testosterone |
| JP2013511973A (ja) * | 2009-11-30 | 2013-04-11 | ファルマツェル、ゲーエムベーハー | 新規７β−ヒドロキシステロイドデヒドロゲナーゼおよびその使用 |
| US8530213B2 (en) | 2009-12-02 | 2013-09-10 | Georgia Tech Research Corporation | Compositions and methods for using NADH oxidases |
| WO2013117251A1 (de) | 2012-02-07 | 2013-08-15 | Annikki Gmbh | Verfahren zur enzymatischen regenerierung von redoxkofaktoren |
| TW201343623A (zh) | 2012-02-07 | 2013-11-01 | Annikki Gmbh | 使氧化還原輔因子經酶催化再生之方法 |
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