The substrate specificity of the heat-stable stereospecific amidase from Klebsiella oxytoca

• Published in: Tetrahedron Vol. 60; no. 3; pp. 747 - 752
• Main Authors: Shaw, Nicholas M, Naughton, Andrew B
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.01.2004; Elsevier
• Subjects: ( R)-(+)-2-Hydroxy-2-(trifluoromethyl)-butanamide; ( R)-(+)-2-Hydroxy-2-(trifluoromethyl)-butanoic acid; ( R)-(+)-3,3,3-Trifluoro-2-amino-2-methylpropionic acid; ( S)-(−)-3,3,3-Trifluoro-2-amino-2-methylpropanamide; Amidase; Biotransformation; Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; ( R)-(+)-3,3,3-Trifluoro-2-amino-2-methylpropionic acid; ( R)-(+)-2-Hydroxy-2-(trifluoromethyl)-butanamide; Biotransformation; ( S)-(−)-3,3,3-Trifluoro-2-amino-2-methylpropanamide; Amidase; ( R)-(+)-2-Hydroxy-2-(trifluoromethyl)-butanoic acid; biotransformation; ACIDS; (R)-(+)-2-hydroxy-2-(trifluoromethyl)-butanoic acid; REACTIVITY; (R)-(+)-2-hydroxy-2-(trifluoromethyl)-butanamide; (S)-(-)-3,3,3-trifluoro-2-amino-2-methylpropanamide; amidase; (R)-(+)-3,3,3-trifluoro-2-amino-2-methylpropionic acid
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2003.10.124

The substrate specificity of the heat-stable stereospecific amidase from Klebsiella oxytoca was investigated. In addition to the original substrate, 3,3,3-trifluoro-2-hydroxy-2-methylpropanamide, the amidase accepted 2-hydroxy-2-(trifluoromethyl)-butanamide and 3,3,3-trifluoro-2-amino-2-methylpropanamide as substrates. Compounds with larger side chains and compounds where the hydroxyl group was substituted with a methoxy group, or in which the CF 3 group was substituted by CCl 3, were not accepted. The biotransformation is a new synthetic route to ( R)-(+)-3,3,3-trifluoro-2-amino-2-methylpropanoic acid, and its related ( S)-(−)-amide, and to ( R)-(+)-2-hydroxy-2-(trifluoromethyl)-butanoic acid and its related ( S)-(−)-amide. Graphic