Lipase-Catalyzed Solid Phase Synthesis of Sugar Esters

✍ Scribed by Cao, Linqiu ;Bornscheuer, Uwe T. ;Schmid, Rolf D.

• Publisher: John Wiley and Sons
• Year: 1996
• Weight: 447 KB
• Volume: 98
• Category: Article
• ISSN: 0931-5985
• DOI: 10.1002/lipi.19960981003

✦ Synopsis

Lipase-catalyzed synthesis of sugar fatty acid esters was performed in a heterogeneous reaction system in the presence of an organic solvent serving as adjuvant. Although the sugar is almost insoluble in such a system, high conversions to the corresponding sugar esters were achieved, due to crystallization of the product. Acylation occurred regioselectively at the primary hydroxyl group and subsequent diacylation was observed only in the case of caprylic acid (2-50,). Best conditions were found for solvents having low log P values and low product solubility such as acetone, using immobilized lipase from Candida antarctica (CAL-8, Novo SP43.5) and fatty acids with chain lengths from CI2 to Cia as acyl donors. The esterification of P-D(+)-gIucose with stearic acid resulted in up to 100% conversion after 48 hours equal to a productivity of 0.4 mmol sugar ester per gram lipase and hour.

Lipase-katalysierte Synthese von Zuckerestern. Die Lipase-katalysierte Synthese von Zucker-Fettsaureestern erfolgte in einem heterogenen Reaktionssystem in Gegenwart eines organischen Losungsrnittels als Adjuvant. Obwohl die Zucker in diesem System nahezu unlosiich sind, wurden hohe Umsetzungen zu den entsprechenden Zuckerestern erzielt, was auf die Kristallisation des Produktes zuriickzufuhren ist. Die Veresterung erfolgte regioselektiv an der primaren Hydroxylgruppe des Zuckers, eine nachfolgende Acylierung zum Diester wurde nur bei Caprylsaure (2-5%) beobachtet. Beste Reakti