Prediction of the equilibrium conversion for the synthesis of acyl hexose through lipase-catalyzed condensation in water-miscible solvent in the presence of molecular sieve.
A method is proposed for predicting the equilibrium conversion for the synthesis of monoacyl hexose through the lipase-catalyzed condensation of a fatty acid and a hexose in a water-miscible solvent in the presence of a molecular sieve, based on the apparent reaction equilibrium constant, the adsorption isotherm of water on the molecular sieve, the solubility of hexose in the solvent, and the mass balance with respect of water. Validity of the model was examined for the syntheses of lauroyl mannose, lauroyl glucose, and myristoyl mannose in acetonitrile, 2-methyl-2-propanol, or 2-methyl-2-butanol with molecular sieves 3A 1/16 and 4A 1/16. The predicted conversions agreed well with the experimental values except for the case where a significant amount of diester was formed as the result of the addition of an excess amount of the molecular sieve to the solvent or the high molar ratio of the fatty acid to the hexose.
Zhang
Xiaoming
X
Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan.
Adachi
Shuji
S
Watanabe
Yoshiyuki
Y
Kobayashi
Takashi
T
Matsuno
Ryuichi
R
D000215:Acylation; D000327:Adsorption; D003198:Computer Simulation; D004789:Enzyme Activation; D004800:Enzymes, Immobilized / Q000737:chemistry; D005227:Fatty Acids / Q000737:chemistry*; D005656:Fungal Proteins; D006601:Hexoses / Q000138:chemical synthesis* / Q000302:isolation & purification; D008049:Lipase / Q000737:chemistry*; D008956:Models, Chemical; D012997:Solvents / Q000737:chemistry; D013379:Substrate Specificity; D014462:Ultrafiltration / Q000379:methods*; D014867:Water / Q000737:chemistry*
D004800:Enzymes, Immobilized; D005227:Fatty Acids; D005656:Fungal Proteins; D006601:Hexoses; D012997:Solvents; D014867:Water; D008049:Lipase; C431349:lipase B, Candida antarctica