Nitrilases catalyze key step to conformationally constrained GABA analogous gamma-amino acids in high optical purity.
Five- and six-membered carbocyclic gamma-amino acids were prepared in high enantiomeric purity by nitrilase-mediated transformation of hitherto unreported gamma-amino nitriles. The nitrilases investigated reveal a strong enantiopreference for cis-isomers (up to 99% ee), whereas trans-isomers were available in up to 86% ee. The biocatalytic enantioselective syntheses of cis-3-aminocyclohexanecarboxylic acid (3b), trans-3-aminocyclohexanecarboxylic acids (4b, 6b, 8b) as well as trans-3-aminocylopentanecarboxylic acid (2b) are hereby reported for the first time.
Winkler
Margit
M
Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 16, A-8010 Graz, Austria.
Knall
Astrid C
AC
Kulterer
Martin R
MR
Klempier
Norbert
N
D000596:Amino Acids / Q000138:chemical synthesis*; D000619:Aminohydrolases / Q000737:chemistry* / Q000378:metabolism; D002384:Catalysis; D006868:Hydrolysis; D013237:Stereoisomerism; D005680:gamma-Aminobutyric Acid / Q000031:analogs & derivatives*
D000596:Amino Acids; D005680:gamma-Aminobutyric Acid; D000619:Aminohydrolases; C021867:nitrilase