The enzymatic resolution of an α-fluoroamide by an acylase

The acylase from Aspergillus melleus was able to hydrolyse the amide bond of (S)-phenylalanine-N-2-(R,S)-fluoropropionamide and discriminate the diastereoisomers such that the (S,S)-diastereoisomer was hydrolysed by an order of magnitude faster than the (S,R)-diasteroisomer. The origin of the kinetic discrimination is attributed to both binding and kinetic effects.