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Journal of Sciences Islamic Republic of Iran، جلد ۳۰، شماره ۱، صفحات ۲۳-۳۱
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عنوان انگلیسی A Crystallization-Induced Asymmetric Transformation using Racemic Phenyl Alanine Methyl Ester Derivatives as Versatile Precursors to Prepare Amino Acids
چکیده انگلیسی مقاله 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.
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نویسندگان مقاله Samira Rahmani-Nezhad |
Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

Shima Dianat |
Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

Abbas Hadjiakhoondi |
Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

نشانی اینترنتی https://jsciences.ut.ac.ir/article_69629_70a9f86ddadef2a437b8810e27d4e0e9.pdf
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