PL433249A1 - Sposób wytwarzania (25R)-spirosta-1,4-dien-3-onu z diosgenonu - Google Patents
Sposób wytwarzania (25R)-spirosta-1,4-dien-3-onu z diosgenonuInfo
- Publication number
- PL433249A1 PL433249A1 PL433249A PL43324920A PL433249A1 PL 433249 A1 PL433249 A1 PL 433249A1 PL 433249 A PL433249 A PL 433249A PL 43324920 A PL43324920 A PL 43324920A PL 433249 A1 PL433249 A1 PL 433249A1
- Authority
- PL
- Poland
- Prior art keywords
- sequence
- buffer
- diosgenone
- activity
- preparation
- Prior art date
Links
- AZXZUBZBLNFUPF-UHFFFAOYSA-N Tamogenone Natural products CC1C(C2(CCC3C4(C)CCC(=O)C=C4CCC3C2C2)C)C2OC11CCC(C)CO1 AZXZUBZBLNFUPF-UHFFFAOYSA-N 0.000 title abstract 4
- AZXZUBZBLNFUPF-CLGLNXEMSA-N chembl1915879 Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCC(=O)C=C4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 AZXZUBZBLNFUPF-CLGLNXEMSA-N 0.000 title abstract 4
- 238000002360 preparation method Methods 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- QEGQIJLALWETNE-CLGLNXEMSA-N (25r)-spirosta-1,4-dien-3-one Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 QEGQIJLALWETNE-CLGLNXEMSA-N 0.000 title abstract 2
- 239000000872 buffer Substances 0.000 abstract 5
- 101710116689 3-oxosteroid 1-dehydrogenase Proteins 0.000 abstract 3
- 102000004190 Enzymes Human genes 0.000 abstract 3
- 108090000790 Enzymes Proteins 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 230000000694 effects Effects 0.000 abstract 3
- CCBICDLNWJRFPO-UHFFFAOYSA-N 2,6-dichloroindophenol Chemical compound C1=CC(O)=CC=C1N=C1C=C(Cl)C(=O)C(Cl)=C1 CCBICDLNWJRFPO-UHFFFAOYSA-N 0.000 abstract 2
- RXGJTUSBYWCRBK-UHFFFAOYSA-M 5-methylphenazinium methyl sulfate Chemical compound COS([O-])(=O)=O.C1=CC=C2[N+](C)=C(C=CC=C3)C3=NC2=C1 RXGJTUSBYWCRBK-UHFFFAOYSA-M 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- 238000006356 dehydrogenation reaction Methods 0.000 abstract 2
- 230000002255 enzymatic effect Effects 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 239000007800 oxidant agent Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- 241000588724 Escherichia coli Species 0.000 abstract 1
- 241000029117 Sterolibacterium denitrificans Species 0.000 abstract 1
- 239000011942 biocatalyst Substances 0.000 abstract 1
- 230000002210 biocatalytic effect Effects 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 abstract 1
- CIJQGPVMMRXSQW-UHFFFAOYSA-M sodium;2-aminoacetic acid;hydroxide Chemical compound O.[Na+].NCC([O-])=O CIJQGPVMMRXSQW-UHFFFAOYSA-M 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- 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
- C12P33/02—Dehydrogenating; Dehydroxylating
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Przedmiotem zgłoszenia jest sposób wytwarzania (25R)-spirosta-1,4-dien-3-onu o wzorze 2, który polega na tym, że prowadzi się regioselektywną enzymatyczną dehydrogenację diosgenonu o wzorze 1 biokatalizatorem w postaci genetycznie zmodyfikowanych komórek E. coli lub preparatem enzymatycznym o aktywności KSTD pochodzącym z bakterii Sterolibacterium denitrificans Chol-1S DSM: 13999 o sekwencji identycznej do Sekwencji 1 lub podobnej do Sekwencji 1 (identyczność nie mniejsza niż 70%) lub z Rodococcus erythropolis SQ1 o sekwencji identycznej do Sekwencji 2 lub podobnej do Sekwencji 2 (identyczność nie mniejsza niż 70%) środowisku wodno-organicznym, w obecności reutleniacza, którym jest 2,6-dichloroindofenol, metosiarczan fenazyny lub mieszanina 2,6-dichloroindofenolu i metosiarczanu fenazyny, w temperaturze 20 - 45°C, w mieszanie reakcyjnej, która zawiera: - bufor zapewniający pH w zakresie 6,5 — 9,0 wybrany spośród potasowego buforu ortofosforanowego, buforu glicyna - wodorotlenek sodu lub buforu chlorowodorku tris(hydroksymetylo)aminometanowego, - wodny roztwór solubilizatora o stężeniu 0 — 10% (w/v), którym jest 2-hydroksypropyl-β-cylkodekstryna, rozpuszczalnik organiczny 2-metoksyetanol, dioksan lub izopropanol w ilości 1 — 4% (v/v), utrzymując biokatalityczną aktywność preparatu enzymatycznego o aktywności KSTD przez okres do 24 godzin, który to proces regioselektywnej dehydrogenacji diosgenonu ma następujący przebieg: do reaktora mieszalnikowego wprowadza się bufor, solubilizator rozpuszczony w wodzie, reutleniacz i diosgenon rozpuszczony w rozpuszczalniku organicznym, po czym inicjuje się reakcję dodając preparat enzymatyczny o aktywności KSTD i monitoruje się przebieg reakcji. Uzyskany w ten sposób produkt oczyszcza się metodą ekstrakcji do fazy stałej.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL433249A PL241477B1 (pl) | 2020-03-13 | 2020-03-13 | Sposób wytwarzania (25R)-spirosta-1,4-dien-3-onu z diosgenonu |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL433249A PL241477B1 (pl) | 2020-03-13 | 2020-03-13 | Sposób wytwarzania (25R)-spirosta-1,4-dien-3-onu z diosgenonu |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL433249A1 true PL433249A1 (pl) | 2021-09-20 |
| PL241477B1 PL241477B1 (pl) | 2022-10-10 |
Family
ID=77746087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL433249A PL241477B1 (pl) | 2020-03-13 | 2020-03-13 | Sposób wytwarzania (25R)-spirosta-1,4-dien-3-onu z diosgenonu |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL241477B1 (pl) |
-
2020
- 2020-03-13 PL PL433249A patent/PL241477B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL241477B1 (pl) | 2022-10-10 |
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