A Crystallization-Induced Asymmetric Transformation using Racemic Phenyl Alanine Methyl Ester Derivatives as Versatile Precursors to Prepare Amino Acids

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Rahmani Nezhad s.; DIANAT SH.; HADJIAKHOONDI A.

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Journal: Journal of Sciences, Islamic Republic of Iran Year:2019 | Volume:30 | Issue:1 Page(s): 23-31

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Title

A Crystallization-Induced Asymmetric Transformation using Racemic Phenyl Alanine Methyl Ester Derivatives as Versatile Precursors to Prepare Amino Acids

Author(s)

Rahmani Nezhad s. | DIANAT SH. | HADJIAKHOONDI A. | Issue Writer Certificate

Keywords

Azlactone

Racemic-phenylalanine methyl ester

Amino acids

Asymmetric transformation

Abstract

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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APA: Copy

Rahmani Nezhad, s., DIANAT, SH., & HADJIAKHOONDI, A.. (2019). 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, 30(1), 23-31. SID. https://sid.ir/paper/729449/en

Vancouver: Copy

Rahmani Nezhad s., DIANAT SH., HADJIAKHOONDI A.. 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[Internet]. 2019;30(1):23-31. Available from: https://sid.ir/paper/729449/en

IEEE: Copy

s. Rahmani Nezhad, SH. DIANAT, and A. HADJIAKHOONDI, “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, vol. 30, no. 1, pp. 23–31, 2019, [Online]. Available: https://sid.ir/paper/729449/en

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