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A Crystallization-Induced Asymmetric Transformation using Racemic Phenyl Alanine Methyl Ester Derivatives as Versatile Precursors to Prepare Amino Acids | ||
| Journal of Sciences, Islamic Republic of Iran | ||
| مقاله 3، دوره 30، شماره 1، فروردین 2019، صفحه 23-31 اصل مقاله (231.67 K) | ||
| نوع مقاله: Original Paper | ||
| شناسه دیجیتال (DOI): 10.22059/jsciences.2019.69629 | ||
| نویسندگان | ||
| Samira Rahmani-Nezhad؛ Shima Dianat؛ Abbas Hadjiakhoondi* | ||
| Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran | ||
| چکیده | ||
| L-Tyrosine and L-Dopa are the precursors in the biological synthesis of amine neurotransmitters. On the other hand, phenylalanine as an aromatic amino acid (AAA) is a precursor in the synthesis of L-Tyrosine and L-Dopa. For some substrates such as amino acids, resolution by the formation of diastereomers offers an attractive alternative. Among different methods in this case, crystallization-induced asymmetric transformation (CIAT) that is in situ racemization and selective crystallization of a reaction product can be a good choice. Using this method, preparation of L-Tyrosine and L-Dopa has been reported. In the synthetic route, racemic phenyl alanine methyl ester derivatives as versatile precursors were prepared by reducing azlactone derivatives with Mg in methanol as a reducing reagent and then in the resolution step (S)- enantiomer of L-Dopa (3,4-dihydroxyphenylalanine) and L-Tyrosine (4-hydroxyphenylalanine) were achieved via salt formation with (2R,3R)-tartaric acid in the presence of 5-nitro salicylaldehyde in good yield and high optical purity. | ||
| کلیدواژهها | ||
| Azlactone؛ Racemic-phenylalanine methyl ester؛ Amino acids؛ Asymmetric transformation | ||
| مراجع | ||
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