4.6 Article

The first direct enzymatic hydrolysis of alicyclic beta-amino esters: A route to enantiopure cis and trans beta-amino acids

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 13, Issue 22, Pages 6397-6401

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200700257

Keywords

amino acids; cispentacin enantioselectivity; enzymes; hydrolysis

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The first direct enzymatic method is reported for the synthesis of cis and trans P-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 iPr(2)O at 65 degrees C. The resolved products, obtained in good yields (>= 42%), could be easily separated.

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