title: Thermo-kinetics of lipase-catalyzed synthesis of 6-O-glucosyldecanoate.
abstract: Lipase-catalyzed synthesis of 6-O-glucosyldecanoate from d-glucose and decanoic acid was performed in dimethyl sulfoxide (DMSO), a mixture of DMSO and tert-butanol and tert-butanol alone with a decreasing order of polarity. The highest conversion yield (> 65%) of decanoic acid was obtained in the blended solvent of intermediate polarity mainly because it could dissolve relatively large amounts of both the reactants. The reaction obeyed Michaelis-Menten type of kinetics. The affinity of the enzyme towards the limiting substrate (decanoic acid) was not affected by the polarity of the solvent, but increased significantly with temperature. The esterification reaction was endothermic with activation energy in the range of 60-67 kJ mol⁻¹. Based on the Gibbs energy values, in the solvent blend of DMSO and tert-butanol the position of the equilibrium was shifted more towards the products compared to the position in pure solvents. Monoester of glucose was the main product of the reaction.
authors.affiliation: Institute of Biological Sciences, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia.
authors.forename: A M
authors.initials: AM
authors.lastname: Gumel
authors.forename: M S M
authors.initials: MS
authors.lastname: Annuar
authors.forename: T
authors.initials: T
authors.lastname: Heidelberg
authors.forename: Y
authors.initials: Y
authors.lastname: Chisti
mesh_terms: D002616:Chemical Engineering / Q000379:methods; D003651:Decanoates / Q000138:chemical synthesis*; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D005656:Fungal Proteins; D005960:Glucosides / Q000138:chemical synthesis*; D007700:Kinetics; D008049:Lipase / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013816:Thermodynamics; D020002:tert-Butyl Alcohol / Q000737:chemistry
chemical_list: D003651:Decanoates; D005656:Fungal Proteins; D005960:Glucosides; D008049:Lipase; C431349:lipase B, Candida antarctica; D020002:tert-Butyl Alcohol; D004121:Dimethyl Sulfoxide