Improved enzymatic syntheses of valuable beta-arylalkyl-beta-amino acid enantiomers.
The enantioselective (E approximately 200) Burkholderia cepacia-catalysed hydrolyses of beta-amino esters with H(2)O (0.5 equiv.) in t-BuOMe or in i-Pr(2)O at 45 degrees C are described. The enantiomers of biologically relevant beta-arylalkyl-substituted beta-amino acids, and especially (R)-3-amino-3-(2,4,5-trifluorophenyl)butanoic acid, the intermediate of the new antidiabetic drug sitagliptine, were prepared with high enantiomeric excesses (ee>or=96%) and in good yields (>or=42%).
Tasnádi
Gábor
G
Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, Hungary.
Forró
Eniko
E
Fülöp
Ferenc
F
D000596:Amino Acids / Q000737:chemistry* / Q000494:pharmacology; D002384:Catalysis; D004789:Enzyme Activation; D007004:Hypoglycemic Agents / Q000138:chemical synthesis*; D004364:Pharmaceutical Preparations / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000596:Amino Acids; D007004:Hypoglycemic Agents; D004364:Pharmaceutical Preparations