SUGAR DERIVATIZATION OF POLYALCOHOLS USING THE FUNGAL ENZYME α-RHAMNOSYL-β-GLUCOSIDASE

MULLER J; FRIES A; BRECCIA JD; MULLER M; MAZZAFERRO L

Santa Rosa

Jornada; XII Jornadas Pampeanas de Ciencias Naturales; 2016

COPROCNA

SUGAR DERIVATIZATION OF POLYALCOHOLS USING THE FUNGAL ENZYME α-RHAMNOSYL-β-GLUCOSIDASE INCITAP-CONICET, FCEyN-Universidad Nacional de La Pampa (UNLPam), Av.Uruguay 151, Santa Rosa, La Pampa, Argentina Institut für Pharmazeutische Wissenschaften, Albert-Ludwigs-Universität Freiburg, Albertstraße 25, 79104 Freiburg, Alemaniamazzaferrolaura@gmail.com The fungal diglycosidase α-rhamnosyl-β-glucosidase has proven to be capable ofcatalyzing transglycosylation reactions using alcohols as sugar acceptors andhesperidin as sugar donor. Glycerol is especially interesting as sugar acceptor, as it is a byproduct of the biodiesel synthesis and thus easily and in vast amounts available.In this work, we tested the polyalcohols ethylene glycol and glycerol as sugaracceptors. Under standard conditions (1.8 mM hesperidin, 40% alcohol, 0.02 U/mLenzyme, 2 h, 60 °C), the corresponding rutinosylated products were obtained (ca.37% conversion regarding hesperidin with glycerol and ca. 52% with ethyleneglycol). By optimizing the reaction conditions (temperature, incubation time, effect of shaking) a conversion higher than 90% was obtained with both acceptors. Since glycerol and ethylene glycol contain multiple alcoholic groups, the transglycosylation products were analyzed using mass spectrometry. In both cases, the enzyme was found to transglycosylate only one alcoholic group. Because of the properties of sugar glycerides, such as protection against oxidative and osmotic stress, they are considered as possible skin-moisturizers and underline the possible use of rutinosylated glycerol in the cosmetic industry.