L-carnitine via enzyme-catalyzed oxidative kinetic resolution.
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.
Ditullio
D
D
School of Pharmacy, University of Wisconsin, Madison 53706.
Anderson
D
D
Chen
C S
CS
Sih
C J
CJ
D016954:Acinetobacter calcoaceticus / Q000235:genetics / Q000254:growth & development / Q000378:metabolism*; D002250:Carbon Radioisotopes; D002331:Carnitine / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D007700:Kinetics; D010084:Oxidation-Reduction; D011865:Radioisotope Dilution Technique; D013237:Stereoisomerism; D013997:Time Factors
D002250:Carbon Radioisotopes; D002331:Carnitine