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KMID : 0043320030260120997
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Archives of Pharmacal Research
2003 Volume.26 No. 12 p.997 ~ p.1001
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Lipase Mediated Chiral Resoulution of 4-Arylthio-2-Butanol as an Intermediate for β-Lactam Antibiotics
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Hwang Kwang-Jin
Baek Chae-Sun
Lee Won-Jae
Kim Hyung-Jin
Lee Jin-Kue
Chin Sung-Min
Moon Chi-Jang
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Abstract
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This paper deals with chiral enzymatic resolution of 4-arylthio-2-butanols by lipase to prepare potential intermediates of -lactam antibiotics. Among several lipases employed, lipase P type enzyme gave the highest ee value to prepare (R)-4-arylthio-2-butyl acetate. The enzymatic resolution of phenyl substituted alcohol (6a) using lipase P showed the highest ee value (99.7%) among those of 4-arylthio-2-butanol derivatives. Lipase P mediated hydrolysis of acylester 7a gave also (R)-alcohol 6a selectively. For determination of enantiomeric purity of these enzymatic resolved analytes, liquid chromatographic analysis was performed using two coupled Chiralcel OD and (R,R)-WhelkO chiral column.
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KEYWORD
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Lipase, 4-Arylthio-2-butanol, Chiral resolution
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