Communications

Enantioselective synthesis of 5-fluoro-L-DOPA via chemoenzymatic route

K. A. Kochetkov^ab, M. A. Tsvetikova^a, O. N. Gorunova^a, N. A. Bystrova^a, V. S. Yufriakov<sup>a

a</sup> A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
^b D.Mendeleev University of Chemical Technology of Russia, Moscow, Russian Federation

Abstract: The title compound, 5-fluoro-3,4-dihydroxy-L-phenylalanine, was prepared in four steps, with the key step having been the enantiospecific production of 5-fluoro-L-tyrosine by the chemoenzymatic reaction between 2-fluorophenol, potassium pyruvate and ammonia promoted by the live culture of Citrobacter freundii cells. 5-Fluoro-L-tyrosine was hydroxylated by sequential nitration, reduction and diazotization followed by hydrolysis.

Keywords: 5-fluoro-L-DOPA, 5-fluoro-L-tyrosine, Chemoenzymatic method, Tyrosin phenol lyase, Enantioselective synthesis, Organofluorine compounds, Amino acids.

Language: English

DOI: 10.1016/j.mencom.2024.01.003

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