title: Albendazole sulfoxide enantiomers: preparative chiral separation and absolute stereochemistry.
abstract: The enantiomeric separation of albendazole sulfoxide was carried out by simulated moving bed chromatography with variable zones (VARICOL). An overall recovery of 97% was achieved and enantiomeric ratios of 99.5% for raffinate and 99.0% for extract were attained. A total of 880 mg of (+)-albendazol sulfoxide and 930 mg of its antipode were collected after 55 cycles or 11 h of process, resulting in a mass rate of 2 g/day. Furthermore the absolute configuration of the enantiopure compounds was determined for the first time by vibrational circular dichroism (VCD) with the aid of theoretical calculations as (-)-(S) and (+)-(R)-albendazole sulfoxide.
authors.affiliation: Chemistry Department, Federal University of São Carlos, P.O. Box 676, São Carlos 13565-905, SP, Brazil.
authors.forename: Tiago C
authors.initials: TC
authors.lastname: Lourenço
authors.forename: João M
authors.initials: JM
authors.lastname: Batista
authors.forename: Maysa
authors.initials: M
authors.lastname: Furlan
authors.forename: Yanan
authors.initials: Y
authors.lastname: He
authors.forename: Laurence A
authors.initials: LA
authors.lastname: Nafie
authors.forename: Cesar C
authors.initials: CC
authors.lastname: Santana
authors.forename: Quezia B
authors.initials: QB
authors.lastname: Cass
mesh_terms: D015766:Albendazole / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification; D002845:Chromatography / Q000379:methods*; D002942:Circular Dichroism; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D015766:Albendazole; C027186:albendazole sulfoxide