Efficient synthesis of 6-O-palmitoyl-1,2-O-isopropylidene-α-D-glucofuranose in an organic solvent system by lipase-catalyzed esterification.
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.
Kobayashi
Takashi
T
Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan. tkoba@kais.kyoto-u.ac.jp
Ehara
Taro
T
Mizuoka
Takanori
T
Adachi
Shuji
S
D000096:Acetone / Q000737:chemistry; D002175:Candida / Q000201:enzymology*; D004800:Enzymes, Immobilized / Q000378:metabolism; D004951:Esterification; D005947:Glucose / Q000031:analogs & derivatives* / Q000378:metabolism; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D019308:Palmitic Acid / Q000378:metabolism; D012997:Solvents; D013696:Temperature; D020002:tert-Butyl Alcohol / Q000737:chemistry
D004800:Enzymes, Immobilized; D012997:Solvents; D000096:Acetone; C028223:1,2-O-isopropylidene-D-glucofuranose; D019308:Palmitic Acid; D008049:Lipase; D005947:Glucose; D020002:tert-Butyl Alcohol