The first direct enzymatic hydrolysis of alicyclic beta-amino esters: a route to enantiopure cis and trans beta-amino acids.
The first direct enzymatic method is reported for the synthesis of cis and trans beta-amino acid enantiomers through the lipase-catalyzed enantioselective hydrolysis of alicyclic beta-amino esters in organic media. High enantioselectivities (E usually >100) were observed when the Candida antarctica lipase B catalyzed reactions were performed with H2O (0.5 equivalents) in iPr2O at 65 degrees C. The resolved products, obtained in good yields (>or=42%), could be easily separated.
Forró
Enikõ
E
Institute of Pharmaceutical Chemistry, University of Szeged, 6701 Szeged, PO Box 427, Hungary.
Fülöp
Ferenc
F
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003510:Cyclohexanes / Q000737:chemistry; D003517:Cyclopentanes / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D006868:Hydrolysis; D008049:Lipase / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism
D000596:Amino Acids; D003510:Cyclohexanes; D003517:Cyclopentanes; D004952:Esters; D008049:Lipase