title: Inexpensive chemical method for preparation of enantiomerically pure phenylalanine.
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.
authors.affiliation: Department of Chemistry, Institute of Chemical Biology and Drug Discovery, State University of New York at Stony Brook, Stony Brook, NY, 11794-3400, USA.
authors.forename: Hiroki
authors.initials: H
authors.lastname: Moriwaki
authors.forename: Daniel
authors.initials: D
authors.lastname: Resch
authors.forename: Hengguang
authors.initials: H
authors.lastname: Li
authors.forename: Iwao
authors.initials: I
authors.lastname: Ojima
authors.forename: Ryosuke
authors.initials: R
authors.lastname: Takeda
authors.forename: José Luis
authors.initials: JL
authors.lastname: Aceña
authors.forename: Vadim
authors.initials: V
authors.lastname: Soloshonok
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic / Q000191:economics / Q000379:methods*; D008024:Ligands; D010649:Phenylalanine / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D008024:Ligands; D010649:Phenylalanine