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

• KAWASAKI Hisashi

  Department of Environmental Materials Science, Tokyo Denki University

• KOYAMA Koutaro

  Department of Environmental Materials Science, Tokyo Denki University

• KUROKAWA Sachio

  Department of Environmental Materials Science, Tokyo Denki University

• WATANABE Kunihiko

  Process Research Department, Aminoscience Laboratories, Ajinomoto Co., Inc.

• NAKAZAWA Masakazu

  Process Research Department, Aminoscience Laboratories, Ajinomoto Co., Inc.

• IZAWA Kunisuke

  Process Research Department, Aminoscience Laboratories, Ajinomoto Co., Inc.

• NAKAMATSU Tsuyoshi

  Department of Environmental Materials Science, Tokyo Denki University

Bibliographic Information

Other Title

• Production of (<i>R</i>)-3-Amino-3-phenylpropionic Acid and (<i>S</i>)-3-Amino-3-phenylpropionic Acid from (<i>R</i>,<i>S</i>)-<i>N</i>-Acetyl-3-amino-3-phenylpropionic Acid Using Microorganisms Having Enantiomer-Specific Amidohydrolyzing Activity

Abstract

(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.<BR>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.

Journal

• Bioscience, Biotechnology, and Biochemistry

  Bioscience, Biotechnology, and Biochemistry 70 (1), 99-106, 2006

  Japan Society for Bioscience, Biotechnology, and Agrochemistry

Keywords

• β-Phe
• <I>N</I>-acetyl-β-Phe
• enantiomer-specific amidohydrolyzing activity
• <I>Variovorax</I>
• <I>Burkholderia</I>

Details

• CRID: 1390001206475428352
• NII Article ID: 10018535147
• NII Book ID: AA10824164
• DOI: 10.1271/bbb.70.99
• ISSN: 13476947
• ISSN: 09168451
• NDL BIB ID: 7791334
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I7791334
• Web Site: http://www.tandfonline.com/doi/pdf/10.1271/bbb.70.99
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed