A divergent chemoenzymatic route to an intermediate for nucleoside analogues.
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.
Basak
Amit
A
Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India. absk@chem.iitkgp.ernet.in
Bisai
Shrabani
S
D002851:Chromatography, High Pressure Liquid; D004798:Enzymes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry
D004798:Enzymes; D009705:Nucleosides