PL404465A1 - Optically pure (+) - (R) -6,4'-dihydroxyflavanone and method of preparing optically pure (+) - (R) -6,4'-dihydroxyflavanone - Google Patents
Optically pure (+) - (R) -6,4'-dihydroxyflavanone and method of preparing optically pure (+) - (R) -6,4'-dihydroxyflavanoneInfo
- Publication number
- PL404465A1 PL404465A1 PL404465A PL40446513A PL404465A1 PL 404465 A1 PL404465 A1 PL 404465A1 PL 404465 A PL404465 A PL 404465A PL 40446513 A PL40446513 A PL 40446513A PL 404465 A1 PL404465 A1 PL 404465A1
- Authority
- PL
- Poland
- Prior art keywords
- dihydroxyflavanone
- optically pure
- strain
- formula
- added
- Prior art date
Links
- MDGCNPDCAJHUOC-OAHLLOKOSA-N (2R)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one Chemical compound OC=1C=C2C(C[C@@H](OC2=CC=1)C1=CC=C(C=C1)O)=O MDGCNPDCAJHUOC-OAHLLOKOSA-N 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 2
- YURQMHCZHLMHIB-UHFFFAOYSA-N 6-methoxy-2-phenyl-2,3-dihydrochromen-4-one Chemical compound C1C(=O)C2=CC(OC)=CC=C2OC1C1=CC=CC=C1 YURQMHCZHLMHIB-UHFFFAOYSA-N 0.000 abstract 2
- 241000228245 Aspergillus niger Species 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- 241000233866 Fungi Species 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 230000017858 demethylation Effects 0.000 abstract 1
- 238000010520 demethylation reaction Methods 0.000 abstract 1
- 230000033444 hydroxylation Effects 0.000 abstract 1
- 238000005805 hydroxylation reaction Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000002609 medium Substances 0.000 abstract 1
- 230000000813 microbial effect Effects 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000013630 prepared media Substances 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 230000009466 transformation Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Przedmiotem wynalazku jest optycznie czysty (+)-(R)-6,4'-dihydroksyflawanon, o wzorze 2 oraz sposób wytwarzania optycznie czystego (+)-(R)-6,4'-dihydroksyflawanonu, o wzorze 2, charakteryzuje sie tym, ze na przygotowana pozywke wprowadza sie szczep Aspergillus Niger MB i w momencie osiagniecia przez grzyb koncowej fazy logarytmicznego wzrostu, dodaje sie 6-metoksyflawanon w ilosci 10 mg na 100 ml pozywki, przy czym proces transformacji mikrobiologicznej prowadzi sie wodna kultura szczepu przy ciaglym wstrzasaniu, w wyniku czego, przy udziale systemu enzymatycznego szczepu, nastepuje demetylacja w pozycji 6, a nastepnie hydroksylacja w pozycji 4' substratu 6-metoksy-flawanonu. Otrzymany produkt ekstrahuje sie rozpuszczalnikiem organicznym niemieszajacym sie z woda i oczyszcza chromatograficznie.The subject of the invention is an optically pure (+)-(R)-6,4'-dihydroxyflavanone of formula 2 and a method for producing optically pure (+)-(R)-6,4'-dihydroxyflavanone of formula 2, characterized by that the Aspergillus Niger MB strain is added to the prepared medium and when the fungus reaches the final phase of logarithmic growth, 6-methoxyflavanone is added in the amount of 10 mg per 100 ml of the medium, while the process of microbial transformation is carried out with water culture of the strain with constant shaking, in resulting in demethylation at the 6-position followed by hydroxylation at the 4' position of the substrate 6-methoxy-flavanone, with the participation of the enzyme system of the strain. The product obtained is extracted with a water-immiscible organic solvent and purified by chromatography.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL404465A PL219974B1 (en) | 2013-06-26 | 2013-06-26 | Optically pure(-)-(S)-6,4'-dihydroxyflavanone and a method for preparing optically pure(+)-(R)-6,4'-dihydroxyflavanone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL404465A PL219974B1 (en) | 2013-06-26 | 2013-06-26 | Optically pure(-)-(S)-6,4'-dihydroxyflavanone and a method for preparing optically pure(+)-(R)-6,4'-dihydroxyflavanone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL404465A1 true PL404465A1 (en) | 2014-01-07 |
| PL219974B1 PL219974B1 (en) | 2015-08-31 |
Family
ID=49877316
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL404465A PL219974B1 (en) | 2013-06-26 | 2013-06-26 | Optically pure(-)-(S)-6,4'-dihydroxyflavanone and a method for preparing optically pure(+)-(R)-6,4'-dihydroxyflavanone |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL219974B1 (en) |
-
2013
- 2013-06-26 PL PL404465A patent/PL219974B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL219974B1 (en) | 2015-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LICE | Declarations of willingness to grant licence |
Effective date: 20150209 |