Enantioselective biotransformations by whole plant cells in natural deep eutectic solvents

U skladu s principima zelene kemije, provedena je ekološki prihvatljiva, enantioselektivna redukcija 1-(3,4-dimetilfenil)-etanona (DMPA) u 1-(R,S)-(3,4-dimetilfenil)-etanol u prirodnim eutektičkim otapalima na bazi kolin-klorida s različitim udjelima vode, primjenom dvije biljne kulture- šećerne repe i kaktusa, kao biokatalizatora. Dobiveni rezultati pokazali su da su konverzija i enantiomerni suvišak, korelirani s udjelom vode i tipom vodikove veze u prirodnom eutektičkom otapalu, dok se (R)-enantiomer alkohola pokazao dominantnim u reakcijama provedenim u većini ispitanih prirodnih eutektičkih otapala. Nadalje, moguće je uspješno provesti tri ciklusa reakcije s istom biljnom biomasom koja se nakon svakog ciklusa reciklira, dok se dobivene konverzije suspstrata u produkt neznatno smanjuju svakim ciklusom. Ispitivanjem biokompatibilnosti prirodnih eutektičkih otapala s biljnim kulturama, pokazalo se da ova otapala uzrokuju permeabilizaciju staničnih membrana, uslijed čega se događaju promjene u metabolizmu biljnih stanica.In accordance to green chemistry principles, an eco-friendly enantioselective reduction of 1-(3,4-dimethylphenyl)ethanol (DMPA) into 1-(R,S)-(3,4-dimethylphenyl)-ethanol was performed in choline chloride-based natural deep eutectic solvents (NADES) with different amounts of water, using two plant callus cultures - sugar beet and cactus as biocatalysts. The obtained results showed that both conversion and enantiomeric excess were found to be correlated with water content and the type of hydrogen bond donor in NADES, with (R)-alcohol configuration being predominate in the reactions conducted in most NADES solutions. Furthermore, it is possible to successfully conduct three cycles of reaction using the same plant biomass that is being recycled after every cycle, with slight decreases in the obtained conversions of substrate into product. In addition, when testing biocompatibility of NADES with plant cells, it was found that NADES are causing permeabilization of the cell membranes, leading to changes in the plant metabolism