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Amino Acids. 2014 Apr;46(4):945-52. doi: 10.1007/s00726-013-1656-0. Epub 2014 Jan 3.

Inexpensive chemical method for preparation of enantiomerically pure phenylalanine.

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1
Department of Chemistry, Institute of Chemical Biology and Drug Discovery, State University of New York at Stony Brook, Stony Brook, NY, 11794-3400, USA.

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.

PMID:
24385244
DOI:
10.1007/s00726-013-1656-0
[Indexed for MEDLINE]
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