[Synthesis of alkyl glycosides, catalyzed by beta-glycosidases in a reversed micelle system].
A basic possibility of enzymic synthesis of alkyl glycosides in a system of the Aerosol-OT (AOT) reverse micelles was studied. Octyl beta-D-galactopyranoside and octyl beta-D-glucopyranoside were synthesized from the corresponding sugars (lactose or glucose) and octyl alcohol under catalysis with glycolytic enzymes, beta-galactosidase and beta-glucosidase, respectively. The transglycosylation/hydrolysis ratio was shifted toward transglycosylation by using octyl alcohol, one of the substrates, as an organic solvent. The alkyl glycosides were thus obtained in one step from a hydrophilic mono- or disaccharide and a hydrophobic aliphatic alcohol. The direction of the reaction was shown to depend on the pH of aqueous solution immobilized in nerves micelles. The maximum yields were 45% and 40% for octyl galactoside and octyl glucoside, respectively; they markedly exceeded the yields of enzymic syntheses in a two-phase system reported previously.
Kuptsova
O S
OS
Department of Chemical Enzymology, Faculty of Chemistry, Moscow State University, Vorob'evy gory, Moscow, 119899 Russia. kuptsova@enz.chem.msu.ru
Kliachko
N L
NL
levashov
A V
AV
D002384:Catalysis; D004143:Dioctyl Sulfosuccinic Acid; D006026:Glycoside Hydrolases / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D006868:Hydrolysis; D007785:Lactose / Q000737:chemistry; D008823:Micelles
D006027:Glycosides; D008823:Micelles; D004143:Dioctyl Sulfosuccinic Acid; D006026:Glycoside Hydrolases; D007785:Lactose