Effective Hydrogenation of 3-(2”-furyl)- and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-prop-2-en-1-one in Selected Yeast Cultures

• Published in: Molecules (Basel, Switzerland) Vol. 24; no. 17; p. 3185
• Main Authors: Łużny, Mateusz, Krzywda, Martyna, Kozłowska, Ewa, Kostrzewa-Susłow, Edyta, Janeczko, Tomasz
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 02.09.2019; MDPI
• Subjects: Biocatalysts; Biotransformation; Cells, Cultured; chalcone; Chalcones - metabolism; Chemical synthesis; Chromatography; dihydrochalcone; Enzymes; Hydrogenation; Microorganisms; Substrate Specificity; sweeteners; Thiophenes - chemical synthesis; Thiophenes - chemistry; Thiophenes - metabolism; Yeast; Yeasts - metabolism; chalcone; biotransformation; sweeteners; dihydrochalcone; yeast
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules24173185

Biotransformations were performed on eight selected yeast strains, all of which were able to selectively hydrogenate the chalcone derivatives 3-(2”-furyl)- (1) and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-prop-2-en-1-one (3) into 3-(2”-furyl)- (2) and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-propan-1-one (4) respectively. The highest efficiency of hydrogenation of the double bond in the substrate 1 was observed in the cultures of Saccharomyces cerevisiae KCh 464 and Yarrowia lipolytica 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 Yarrowia lipolytica 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.