Toksičnost aromatskih ketona za stanice kvasca i ubrzanje njihove redukcije primjenom adsorpcijskih smola

Asymmetric reduction of the prochiral aromatic ketone catalyzed by yeast cells is one of the most promising routes to produce its corresponding enantiopure aromatic alcohol, but the space-time yield does not meet people’s expectations. Therefore, the toxicity of aromatic ketone and aromatic alcohol to the yeast cell is investigated in this work. It has been found that the aromatic compounds are poisonous to the yeast cell. The activity of yeast cell decreases steeply when the concentration of acetophenone (ACP) is higher than 30.0 mmol/L. Asymmetric reduction of acetophenone to chiral S-α-phenylethyl alcohol (PEA) catalyzed by the yeast cell was chosen as the model reaction to study in detail the promotion effect of the introduction of the resin adsorption on the asymmetric reduction reaction. The resin acts as the substrate reservoir and product extraction agent in situ. It has been shown that this reaction could be remarkably improved with this technique when the appropriate kind of resin is applied. The enantioselectivity and yield are acceptable even though the initial ACP concentration reaches 72.2 mmol/L.Asimetrična redukcija prokiralnih aromatskih ketona, katalizirana stanicama kvasca, obećavajuća je metoda proizvodnje enantiomerno čistih aromatskih alkohola, no iskorištenje reakcije ne zadovoljava današnje potrebe. U radu je utvrđena toksičnost aromatskih ketona i alkohola za stanice kvasca. Aktivnost stanica kvasca naglo se smanjila pri koncentracijama acetofenona većim od 30 mmol/L. Kao model reakcije za detaljno ispitivanje pozitivnog učinka uvođenja adsorpcijskih smola odabrana je asimetrična redukcija acetofenona u kiralni S-α-feniletilni alkohol, katalizirana stanicama kvasca. Utvrđeno je da smola djeluje kao rezervoar supstrata i agens za ekstrakciju proizvoda in situ. Tako se odvijanje reakcije može znatno poboljšati uvođenjem prikladne smole. Enantioselektivnost i prinos su zadovoljavajući iako je početna koncentracija acetofenona dosegla čak 72,2 mmol/L