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

(R)-3-Amino-3-phenylpropionic acid ((R)-β-Phe) and (S)-3-amino-3-phenylpropionic acid ((S)-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 N-...

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Bibliographic Details
Published in:	Bioscience, biotechnology, and biochemistry Vol. 70; no. 1; pp. 99 - 106
Main Authors:	KAWASAKI, Hisashi, KOYAMA, Koutaro, KUROKAWA, Sachio, WATANABE, Kunihiko, NAKAZAWA, Masakazu, IZAWA, Kunisuke, NAKAMATSU, Tsuyoshi
Format:	Journal Article
Language:	English
Published:	Tokyo Japan Society for Bioscience, Biotechnology, and Agrochemistry 01-01-2006 Japan Society for Bioscience Biotechnology and Agrochemistry Oxford University Press
Subjects:	Biological and medical sciences Burkholderia Cell-Free System enantiomer-specific amidohydrolyzing activity Fundamental and applied biological sciences. Psychology Hydrogen-Ion Concentration Hydrolysis N-acetyl-β-Phe Phenylalanine - analogs & derivatives Phenylalanine - biosynthesis Phenylalanine - chemistry Soil Microbiology Stereoisomerism Substrate Specificity Temperature Variovorax β-Phe N-acetyl-β-Phe Aminoacid Enantiomer Production Variovorax Bacteria β-Phe Burkholderia Microorganism enantiomer-specific amidohydrolyzing activity
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Summary:	(R)-3-Amino-3-phenylpropionic acid ((R)-β-Phe) and (S)-3-amino-3-phenylpropionic acid ((S)-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 N-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 (R,S)-N-acetyl-3-amino-3-phenylpropionic acid ((R,S)-N-Ac-β-Phe) in an enantiomer-specific manner was performed. A microorganism having (R)-enantiomer-specific amidohydrolyzing activity and another having both (R)-enantiomer- and (S)-enantiomer-specific amidohydrolyzing activities were obtained from soil samples. Using 16S rDNA analysis, the former organism was identified as Variovorax sp., and the latter as Burkholderia sp. Using these organisms, enantiomerically pure (R)-β-Phe (>99.5% ee) and (S)-β-Phe (>99.5% ee) with a high molar conversion yield (67%-96%) were obtained from the racemic substrate.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0916-8451 1347-6947
DOI:	10.1271/bbb.70.99