title: Deep eutectic solvents (DESs) are viable cosolvents for enzyme-catalyzed epoxide hydrolysis.
abstract: A special group of ionic liquids, deep eutectic solvents (DESs) have been tested as cosolvents in enzyme-catalyzed hydrolysis of a chiral (1,2)-trans-2-methylstyrene oxide. The choline chloride:ethane diol (ET), choline chloride:glycerol (GLY) and choline:chloride:urea (REL) DESs were included in the reaction mixtures with epoxide and the potato epoxide hydrolase StEH1. The effect of the DESs on enzyme function was primarily elevations of K(M) (up to 20-fold) and with lesser effects on turnover numbers (twofold variation). The regioselectivity in hydrolysis of the (1R,2R)-2-trans-methylstyrene oxide was altered in the presence of GLY or ET to favor epoxide ring opening at the benzylic carbon (R=2.33), enhancing the regioselectivity observed in buffer-only systems (R=1.35). The DES solutions dissolved 1.5-fold higher epoxide concentrations as compared to phosphate buffer. The total conversion of high concentration (40 g/l) of (1S,2S)-MeSO was not negatively affected by addition of 40% GLY.
authors.affiliation: Department of Biochemistry and Organic Chemistry, Uppsala University, Box 576, SE-75123 Uppsala, Sweden.
authors.forename: Diana
authors.initials: D
authors.lastname: Lindberg
authors.forename: Mario
authors.initials: M
authors.lastname: de la Fuente Revenga
authors.forename: Mikael
authors.initials: M
authors.lastname: Widersten
mesh_terms: D055162:Biocatalysis; D004851:Epoxide Hydrolases / Q000378:metabolism*; D004852:Epoxy Compounds / Q000737:chemistry / Q000378:metabolism*; D006207:Half-Life; D006868:Hydrolysis; D052578:Ionic Liquids / Q000378:metabolism*; D007700:Kinetics; D011198:Solanum tuberosum / Q000201:enzymology*; D012997:Solvents / Q000378:metabolism*; D013237:Stereoisomerism; D013343:Styrenes / Q000737:chemistry / Q000378:metabolism; D013379:Substrate Specificity
chemical_list: C434341:2-methylstyrene oxide; D004852:Epoxy Compounds; D052578:Ionic Liquids; D012997:Solvents; D013343:Styrenes; D004851:Epoxide Hydrolases