Skip to main navigation Skip to search Skip to main content

Inexpensive chemical method for preparation of enantiomerically pure phenylalanine

  • Hiroki Moriwaki
  • , Daniel Resch
  • , Hengguang Li
  • , Iwao Ojima
  • , Ryosuke Takeda
  • , José Luis Aceña
  • , Vadim Soloshonok
  • Stony Brook University
  • Hamari Chemicals, Ltd.
  • University of the Basque Country
  • Ikerbasque Basque Foundation for Science

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Here, we report the most inexpensive procedure for chemical synthesis of enantiomerically pure phenylalanine. As a source of chirality, we use the ultimately inexpensive chiral auxiliary, 1-(phenyl)ethylamine, incorporated into the specially designed ligands which form the corresponding intermediate Ni(II) complexes with racemic phenylalanine. Diastereomerically pure Ni(II) complexes, containing either (S)- or (R)-phenylalanine, were disassembled to produce enantiomerically pure target amino acid, along with recycling the chiral ligand. All reactions were conducted under operationally convenient conditions, featuring high yields and thus underscoring attractive cost structure of this method.

Original languageEnglish
Pages (from-to)945-952
Number of pages8
JournalAmino Acids
Volume46
Issue number4
DOIs
StatePublished - Apr 1 2014

Keywords

  • Asymmetric synthesis
  • Ni(II) complexes
  • Phenylalanine
  • Schiff bases
  • Stereogenic nitrogen

Fingerprint

Dive into the research topics of 'Inexpensive chemical method for preparation of enantiomerically pure phenylalanine'. Together they form a unique fingerprint.

Cite this