title: Chirality Control in Enzyme-Catalyzed Dynamic Kinetic Resolution of 1,3-Oxathiolanes.
abstract: The origin of enantioenrichment in enzyme-catalyzed dynamic kinetic resolution of 1,3-oxathiolane derivatives, key intermediates for asymmetric lamivudine synthesis, was elucidated. The chirality control could be determined by chiral HPLC and NOE NMR spectroscopy using a modified 1,3-oxathiolane compound obtained through enzyme-catalyzed selective hydrolysis. Solvent-dependent stereoselectivity was observed under biphasic conditions using different organic solvents with phosphate buffer.
authors.affiliation: Department of Chemistry, KTH - Royal Institute of Technology, Teknikringen 30, Stockholm S-10044, Sweden.
authors.forename: Lei
authors.initials: L
authors.lastname: Hu
authors.affiliation: Department of Chemistry, KTH - Royal Institute of Technology, Teknikringen 30, Stockholm S-10044, Sweden.
authors.forename: Yansong
authors.initials: Y
authors.lastname: Ren
authors.affiliation: Department of Chemistry, KTH - Royal Institute of Technology, Teknikringen 30, Stockholm S-10044, Sweden.
authors.forename: Olof
authors.initials: O
authors.lastname: Ramström
mesh_terms: D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D007700:Kinetics; D019259:Lamivudine / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D055601:Organic Chemistry Phenomena; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013876:Thiophenes / Q000737:chemistry*
chemical_list: D012997:Solvents; D013876:Thiophenes; C013177:1,3-oxathiolane; D019259:Lamivudine