title: Lipase mediated chiral resolution of 4-arylthio-2-butanol as an intermediate for beta-lactam antibiotics.
abstract: This paper deals with chiral enzymatic resolution of 4-arylthio-2-butanols by lipase to prepare potential intermediates of beta-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.
authors.affiliation: Department of Chemical System Engineering, Hongik University, Jochiwon, Chungnam 339-701, Korea. kjhwang@wow.hongik.ac.kr
authors.forename: Kwang-Jin
authors.initials: KJ
authors.lastname: Hwang
authors.forename: Jinkue
authors.initials: J
authors.lastname: Lee
authors.forename: Sungmin
authors.initials: S
authors.lastname: Chin
authors.forename: Chi Jang
authors.initials: CJ
authors.lastname: Moon
authors.forename: Wonjae
authors.initials: W
authors.lastname: Lee
authors.forename: Chae-Sun
authors.initials: CS
authors.lastname: Baek
authors.forename: Hyung Jin
authors.initials: HJ
authors.lastname: Kim
mesh_terms: D000440:Butanols / Q000032:analysis / Q000138:chemical synthesis*; D008049:Lipase / Q000032:analysis / Q000138:chemical synthesis*; D013237:Stereoisomerism; D047090:beta-Lactams / Q000032:analysis / Q000138:chemical synthesis*
chemical_list: D000440:Butanols; D047090:beta-Lactams; C043958:2-butanol; D008049:Lipase