title: A divergent chemoenzymatic route to an intermediate for nucleoside analogues.
abstract: Two regioisomeric isoxazoline monoacetates 1 and 2 were synthesized from the corresponding diacetate 3 via PPL or PLE catalyzed hydrolysis. With both the enzymes, the initial regioselectivity (approximately 3-4:1) was offset by an intramolecular acyl transfer. In addition to a non-enzymatic catalysis for the acyl transfer, preliminary experiments do suggest a definite but minor role of enzyme for this intramolecular acyl transfer. Compounds 1 and 2 may serve as intermediates for nucleoside analogues.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India. absk@chem.iitkgp.ernet.in
authors.forename: Amit
authors.initials: A
authors.lastname: Basak
authors.forename: Shrabani
authors.initials: S
authors.lastname: Bisai
mesh_terms: D002851:Chromatography, High Pressure Liquid; D004798:Enzymes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004798:Enzymes; D009705:Nucleosides