Simultaneous enzymatic synthesis of (S)-3-fluoroalanine and (R)-3-fluorolactic acid

A coupled enzymatic system for the simultaneous synthesis of (S)-3-fluoroalanine (1a) and (R)-3-fluorolactic acid (3) with L-alanine dehydrogenase (L-AlaDH) from Bacillus subtilis and rabbit muscle L-lactate dehydrogenase (L-LDH) using rac-1 and NAD(+) is described. Analysis of isolated products of the laboratory preparative scale process revealed la in 60% yield and 88% ee and 3 in 80% yield and over 99% ee. The compounds la and 3 represent chiral building blocks for the synthesis of several products with pharmacological activity. (C) 2000 Elsevier Science Ltd. All rights reserved.