Cyclic resolution of racemic ibuprofen via coupled efficient lipase and acid-base catalysis.
Extracellular lipase LIP prepared in our lab from the yeast Yarrowia lipolytica was used for the resolution of racemic ibuprofen. The (S)-enantiomer was preferred by lipase LIP, and the unreacted (R)-enantiomer was extracted and racemized in basic solvent-water medium to be re-resolved. Solvent, content of solvent, base concentration, and temperature have a strong effect on racemization. The (S)-ester was separated and hydrolyzed to (S)-ibuprofen in acidic dimethyl sulfoxide-water mixture containing 70% dimethyl sulfoxide. The high purity (S)-ibuprofen (ee = 0.98) was obtained using lipase LIP to catalyze hydrolysis of (S)-ester in 0.1 M phosphate buffer (pH = 8).
School of Life Science and Technology, Beijing University of Chemical Technology, Beijing, 100029, China.
Ying
Y
Liu
Fang
F
Wang
Tianwei
T
Tan
D055162:Biocatalysis; D002021:Buffers; D004952:Esters / Q000737:chemistry; D019855:Ethylene Glycol / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D007052:Ibuprofen / Q000737:chemistry* / Q000378:metabolism; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D010710:Phosphates / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D013696:Temperature; D014867:Water / Q000737:chemistry; D025062:Yarrowia / Q000201:enzymology*
D002021:Buffers; D004952:Esters; D010710:Phosphates; D012997:Solvents; D014867:Water; D008049:Lipase; D019855:Ethylene Glycol; D007052:Ibuprofen