N-Phenylacetyl derivatives of beta-fluoroalkyl-beta-alanines 6 were sy
nthesized and biocatalytically resolved to the corresponding enantiopu
re beta-amino acids 7, 9 with the aid of penicillin acylase (EC 3.5.1.
11) from Escherichia coli. In substrates 6 the enantioselectivity of t
he biocatalytic process was practically uninfluenced by the nature of
the fluoroalkyl chain. Thus, beta-fluoroalkyl-beta-alanines 7, 9 beari
ng short (R = CF3, CHF2) or long [C3F7, H(CF2)(4)] chains were prepare
d in high enantiomeric purity. The (R)-enantiomer was the fast-reactin
g enantiomer in all cases.