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L-carnitine via enzyme-catalyzed oxidative kinetic resolution
D Ditullio1, D Anderson, C S Chen
1School of Pharmacy, University of Wisconsin, Madison 53706.
Bioorganic & Medicinal Chemistry
|June 1, 1994
Summary
High optical purity L-carnitine was produced using a mutant Acinetobacter strain. This microorganism selectively metabolized D-carnitine, yielding L-carnitine with 93% recovery and 92% enantiomeric excess.
Area of Science:
- Biotechnology
- Microbial Metabolism
- Biocatalysis
Background:
- L-Carnitine is vital for fatty acid metabolism.
- Efficient production of enantiomerically pure L-carnitine is challenging.
- Microbial kinetic resolution offers a sustainable approach.
Purpose of the Study:
- To develop a method for producing high optical purity L-carnitine.
- To investigate the microbial metabolism of DL-carnitine.
- To identify the metabolic pathway and byproducts.
Main Methods:
- Utilized a mutant strain of Acinetobacter calcoaceticus ATCC 39647 for kinetic resolution.
- Performed stereoselective metabolism of DL-carnitine.
- Analyzed degradation products and enantiomeric excess.
Main Results:
- Achieved 93% recovery of L-carnitine with 92% enantiomeric excess.
- Identified preferential metabolism of the D-enantiomer by the microorganism.
- Determined the degradation pathway involves monooxygenase-catalyzed oxidative cleavage.
Conclusions:
- Acinetobacter calcoaceticus mutant effectively produces enantiomerically pure L-carnitine.
- The stereoselective metabolism is likely due to differential cell membrane permeability.
- This method provides a high-yield, high-purity route for L-carnitine production.