Efficient synthesis of 6-O-palmitoyl-1,2-O-isopropylidene-α-D-glucofuranose in an organic solvent system by lipase-catalyzed esterification.

• Main Authors: Kobayashi, Takashi, Ehara, Taro, Mizuoka, Takanori, Adachi, Shuji
• Other Authors: 小林, 敬
• Format: Article in Journal/Newspaper
• Language: English
• Published: 2010
• Subjects: Esterification; Lipase; Solvent mixture; Sugar acetal; Sugar ester; Antarc*; Antarctica
• Online Access: http://hdl.handle.net/2433/131829

In order to synthesize a sugar ester at high concentration, 1, 2-O-isopropylidene-α-D-glucofuranose (IpGlc), which is one of the sugar acetals and is more hydrophobic than unmodified glucose, was esterified with palmitic acid at 40°C using immobilized lipase from Candida antarctica in some organic solvents or their mixtures. Acetone + t-butyl alcohol (3:1 v/v) improved both the initial reaction rate and yield after 80 h: the product reached its maximum value (240 mmol/kg solvent; ca. 110 g/kg solvent) when 400 mmol IpGlc/kg solvent and 1, 200 mmol palmitic acid/kg solvent were used in this solvent mixture.