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

Biotechnol Lett. 2010 Nov;32(11):1679-84. doi: 10.1007/s10529-010-0334-5. Epub 2010 Jun 24.

Abstract

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.

MeSH terms

  • Acetone / chemistry
  • Candida / enzymology*
  • Enzymes, Immobilized / metabolism
  • Esterification
  • Glucose / analogs & derivatives*
  • Glucose / metabolism
  • Kinetics
  • Lipase / metabolism*
  • Palmitic Acid / metabolism
  • Solvents
  • Temperature
  • tert-Butyl Alcohol / chemistry

Substances

  • Enzymes, Immobilized
  • Solvents
  • Acetone
  • 1,2-O-isopropylidene-D-glucofuranose
  • Palmitic Acid
  • Lipase
  • Glucose
  • tert-Butyl Alcohol