Inexpensive chemical method for preparation of enantiomerically pure phenylalanine

• Published in: Amino acids Vol. 46; no. 4; pp. 945 - 952
• Main Authors: Moriwaki, Hiroki, Resch, Daniel, Li, Hengguang, Ojima, Iwao, Takeda, Ryosuke, Aceña, José Luis, Soloshonok, Vadim
• Format: Journal Article
• Language: English
• Published: Vienna Springer-Verlag 01-04-2014; Springer Vienna; Springer Nature B.V
• Subjects: Amino acids; Amino Acids - chemistry; Analytical Chemistry; Biochemical Engineering; Biochemistry; Biomedical and Life Sciences; Chemistry Techniques, Synthetic - economics; Chemistry Techniques, Synthetic - methods; Chirality; Dismantling; Life Sciences; Ligands; Neurobiology; nickel; Original Article; Phenylalanine; Phenylalanine - chemical synthesis; Phenylalanine - chemistry; Proteomics; Recycling; Stereoisomerism; Synthesis; yields; Stereogenic nitrogen; Schiff bases; Phenylalanine; Asymmetric synthesis; Ni(II) complexes
• ISSN: 0939-4451; 1438-2199
• DOI: 10.1007/s00726-013-1656-0

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.