Production of (R)-3-Amino-3-phenylpropionic Acid and (S)-3-Amino-3-phenylpropionic Acid from (R,S)-N-Acetyl-3-amino-3-phenylpropionic Acid Using Microorganisms Having Enantiomer-Specific Amidohydrolyzing Activity
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(<I>R</I>)-3-Amino-3-phenylpropionic acid ((<I>R</I>)-β-Phe) and (<I>S</I>)-3-amino-3-phenylpropionic acid ((<I>S</I>)-β-Phe) are key compounds on account of their use as intermediates in synthesizing pharmaceuticals. Enantiomerically pure non-natural amino acids are generally prepared by enzymatic resolution of the racemic <I>N</I>-acetyl form, but despite the intense efforts this method could not be used for preparing enantiomerically pure β-Phe, because the effective enzyme had not been found. Therefore, screening for microorganisms capable of amidohydrolyzing (<I>R</I>,<I>S</I>)-<I>N</I>-acetyl-3-amino-3-phenylpropionic acid ((<I>R</I>,<I>S</I>)-<I>N</I>-Ac-β-Phe) in an enantiomer-specific manner was performed.<BR>A microorganism having (<I>R</I>)-enantiomer-specific amidohydrolyzing activity and another having both (<I>R</I>)-enantiomer- and (<I>S</I>)-enantiomer-specific amidohydrolyzing activities were obtained from soil samples. Using 16S rDNA analysis, the former organism was identified as <I>Variovorax</I> sp., and the latter as <I>Burkholderia</I> sp. Using these organisms, enantiomerically pure (<I>R</I>)-β-Phe (>99.5% ee) and (<I>S</I>)-β-Phe (>99.5% ee) with a high molar conversion yield (67%–96%) were obtained from the racemic substrate.
- Agricultural and Biological Chemistry
Agricultural and Biological Chemistry 70(1), 99-106, 2006-01-23
Japan Society for Bioscience, Biotechnology, and Agrochemistry