Abstract
l-Carnitine of high optical purity was prepared via kinetic resolution using a mutant strain of Acinetobacter calcoaceticus ATCC 39647, This organism preferentially metabolized the d-enantiomer of the racemate to furnish l-carnitine. Recovery of l-carnitine was 93 %, providing a total weight yield of 46.5 % in 92% enantiomeric excess. The mode of degradation of carnitine was shown to proceed via a monooxygenase-catalyzed oxidative cleavage resulting in the formation of trimethylamine and malic acid. The data suggest that the stereoselective metabolism of dl-carnitine is probably the result of differential permeability of the cell membrane towards the optical antipodes.
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