Effective Hydrogenation of 3-(2”-furyl)- and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-prop-2-en-1-one in Selected Yeast Cultures
Biotransformations were performed on eight selected yeast strains, all of which were able to selectively hydrogenate the chalcone derivatives 3-(2”-furyl)- (<b>1</b>) and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-prop-2-en-1-one (<b>3</b>) into 3-(2&am...
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| Format: | Article |
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MDPI AG
2019-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/17/3185 |
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| author | Mateusz Łużny Martyna Krzywda Ewa Kozłowska Edyta Kostrzewa-Susłow Tomasz Janeczko |
| author_facet | Mateusz Łużny Martyna Krzywda Ewa Kozłowska Edyta Kostrzewa-Susłow Tomasz Janeczko |
| author_sort | Mateusz Łużny |
| collection | DOAJ |
| description | Biotransformations were performed on eight selected yeast strains, all of which were able to selectively hydrogenate the chalcone derivatives 3-(2”-furyl)- (<b>1</b>) and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-prop-2-en-1-one (<b>3</b>) into 3-(2”-furyl)- (<b>2</b>) and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-propan-1-one (<b>4</b>) respectively. The highest efficiency of hydrogenation of the double bond in the substrate <b>1</b> was observed in the cultures of <i>Saccharomyces cerevisiae</i> KCh 464 and <i>Yarrowia lipolytica</i> KCh 71 strains. The substrate was converted into the product with > 99% conversion just in six hours after biotransformation started. The compound containing the sulfur atom in its structure was most effectively transformed by the <i>Yarrowia lipolytica</i> KCh 71 culture strain (conversion > 99%, obtained after three hours of substrate incubation). Also, we observed that, different strains of tested yeasts are able to carry out the bioreduction of the used substrate with different yields, depending on the presence of induced and constitutive ene reductases in their cells. The biggest advantage of this process is the efficient production of one product, practically without the formation of side products. |
| first_indexed | 2024-12-10T22:59:46Z |
| format | Article |
| id | doaj.art-5f32684fe67442628dbe0d9ca381065e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-10T22:59:46Z |
| publishDate | 2019-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-5f32684fe67442628dbe0d9ca381065e2022-12-22T01:30:10ZengMDPI AGMolecules1420-30492019-09-012417318510.3390/molecules24173185molecules24173185Effective Hydrogenation of 3-(2”-furyl)- and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-prop-2-en-1-one in Selected Yeast CulturesMateusz Łużny0Martyna Krzywda1Ewa Kozłowska2Edyta Kostrzewa-Susłow3Tomasz Janeczko4Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandDepartment of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandDepartment of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandDepartment of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandDepartment of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandBiotransformations were performed on eight selected yeast strains, all of which were able to selectively hydrogenate the chalcone derivatives 3-(2”-furyl)- (<b>1</b>) and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-prop-2-en-1-one (<b>3</b>) into 3-(2”-furyl)- (<b>2</b>) and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-propan-1-one (<b>4</b>) respectively. The highest efficiency of hydrogenation of the double bond in the substrate <b>1</b> was observed in the cultures of <i>Saccharomyces cerevisiae</i> KCh 464 and <i>Yarrowia lipolytica</i> KCh 71 strains. The substrate was converted into the product with > 99% conversion just in six hours after biotransformation started. The compound containing the sulfur atom in its structure was most effectively transformed by the <i>Yarrowia lipolytica</i> KCh 71 culture strain (conversion > 99%, obtained after three hours of substrate incubation). Also, we observed that, different strains of tested yeasts are able to carry out the bioreduction of the used substrate with different yields, depending on the presence of induced and constitutive ene reductases in their cells. The biggest advantage of this process is the efficient production of one product, practically without the formation of side products.https://www.mdpi.com/1420-3049/24/17/3185biotransformationchalconedihydrochalconeyeastsweeteners |
| spellingShingle | Mateusz Łużny Martyna Krzywda Ewa Kozłowska Edyta Kostrzewa-Susłow Tomasz Janeczko Effective Hydrogenation of 3-(2”-furyl)- and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-prop-2-en-1-one in Selected Yeast Cultures Molecules biotransformation chalcone dihydrochalcone yeast sweeteners |
| title | Effective Hydrogenation of 3-(2”-furyl)- and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-prop-2-en-1-one in Selected Yeast Cultures |
| title_full | Effective Hydrogenation of 3-(2”-furyl)- and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-prop-2-en-1-one in Selected Yeast Cultures |
| title_fullStr | Effective Hydrogenation of 3-(2”-furyl)- and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-prop-2-en-1-one in Selected Yeast Cultures |
| title_full_unstemmed | Effective Hydrogenation of 3-(2”-furyl)- and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-prop-2-en-1-one in Selected Yeast Cultures |
| title_short | Effective Hydrogenation of 3-(2”-furyl)- and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-prop-2-en-1-one in Selected Yeast Cultures |
| title_sort | effective hydrogenation of 3 2 furyl and 3 2 thienyl 1 2 hydroxyphenyl prop 2 en 1 one in selected yeast cultures |
| topic | biotransformation chalcone dihydrochalcone yeast sweeteners |
| url | https://www.mdpi.com/1420-3049/24/17/3185 |
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