title: Dual effect of benzyl alcohol on α-glucosidase activity: efficient substrate for high yield transglucosylation and non-competitive inhibitor of its hydrolytic activity.
abstract: Benzyl alcohol, a potent anesthetic and bacteriostatic, can be efficiently glucosylated by α-glucosidase from Saccharomyces cerevisiae to produce benzyl alcohol α-glucoside with a 75% yield. However, while studying the transglucosylation reaction conditions, it was found out that benzyl alcohol is a non-competitive inhibitor of α-glucosidase's hydrolytic activity (Ki=18mM, toward maltose). Due to its interesting ability to be glycosylated by the enzyme and to inhibit its hydrolytic activity, we proposed a plausible mechanism for the phenolic α-glucosydase inhibitor's binding, since the mechanism of inhibition has not yet been elucidated.
authors: Faculty of Chemistry, University of Belgrade, Studentski trg 12, 11000 Belgrade, Serbia.
authors: Marija
authors: M
authors: Pavlović
authors: Faculty of Chemistry, University of Belgrade, Studentski trg 12, 11000 Belgrade, Serbia. Electronic address: adimitrijevic@chem.bg.ac.rs.
authors: Aleksandra
authors: A
authors: Dimitrijević
authors: Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11000 Belgrade, Serbia.
authors: Dejan
authors: D
authors: Bezbradica
authors: Faculty of Chemistry, University of Belgrade, Studentski trg 12, 11000 Belgrade, Serbia.
authors: Nenad
authors: N
authors: Milosavić
authors: Faculty of Chemistry, University of Belgrade, Studentski trg 12, 11000 Belgrade, Serbia.
authors: Marija
authors: M
authors: Gavrović-Jankulović
authors: Faculty of Chemistry, University of Belgrade, Studentski trg 12, 11000 Belgrade, Serbia.
authors: Dejan
authors: D
authors: Šegan
authors: Faculty of Chemistry, University of Belgrade, Studentski trg 12, 11000 Belgrade, Serbia.
authors: Dušan
authors: D
authors: Veličković
mesh_terms: D019905:Benzyl Alcohol / Q000737:chemistry*; D065089:Glycoside Hydrolase Inhibitors; D006031:Glycosylation; D006868:Hydrolysis; D008320:Maltose / Q000737:chemistry; D011485:Protein Binding; D012441:Saccharomyces cerevisiae / Q000201:enzymology*; D013379:Substrate Specificity; D013696:Temperature; D000520:alpha-Glucosidases / Q000737:chemistry* / Q000378:metabolism
chemical_list: D065089:Glycoside Hydrolase Inhibitors; D008320:Maltose; D000520:alpha-Glucosidases; D019905:Benzyl Alcohol
keywords: Benzyl alcohol; Primary hydrolysis; Transglucosylation; α-Glucosidase inhibition