• Media type: E-Article
  • Title: Synthesis of Stereospecifically Deuterated Phenylalanines and Determination of Their Configuration
  • Contributor: BARTL, Knut; CAVALAR, Christiane; KREBS, Traute; RIPP, Engelbert; RÉTEY, János; HULL, William E.; GÜNTHER, Helmut; SIMON, Helmut
  • imprint: Wiley, 1977
  • Published in: European Journal of Biochemistry
  • Language: English
  • DOI: 10.1111/j.1432-1033.1977.tb11246.x
  • ISSN: 1432-1033; 0014-2956
  • Keywords: Biochemistry
  • Origination:
  • Footnote:
  • Description: <jats:p> <jats:list list-type="explicit-label"> <jats:list-item><jats:p>Starting from <jats:italic>trans</jats:italic>‐cinnamic acid a chiral (−)3‐phenyl‐[2,3‐<jats:sup>2</jats:sup>H]propionic acid has been synthesized using <jats:italic>Clostridium kluyveri</jats:italic> cells as catalyst.</jats:p></jats:list-item> <jats:list-item><jats:p>The chiral dideuterated acid has been converted by chemical methods to a mixture of (2R) and (2S)‐phenyl[2,3‐<jats:sup>2</jats:sup>H]‐alanine.</jats:p></jats:list-item> <jats:list-item><jats:p>By means of <jats:sup>1</jats:sup>H nuclear magnetic resonance spectroscopy and the action of D and L‐amino‐acid oxidase the configuration of the phenylalanine has been shown to be (2<jats:italic>R</jats:italic>, 3<jats:italic>S</jats:italic>) and (2<jats:italic>S</jats:italic>, 3<jats:italic>S</jats:italic>), respectively. The labelled phenylalanine is thus sterically and isotopically homogeneous at position 3 but heterogeneous at position 2.</jats:p></jats:list-item> </jats:list> </jats:p>
  • Access State: Open Access