Biocatalytic resolution of β-fluoroalkyl-β-amino acids

Vadim A. Soloshonok, Alexander G. Kirilenko, Nataly A. Fokina, Irine P. Shishkina, Sergey V. Galushko, Valery P. Kukhar, Vytas K. Švedas, Elena V. Kozlova

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    77 Citations (Scopus)

    Abstract

    N-Phenylacetyl derivatives of β-fluoroalkyl-β-alanines 6 were synthesized and biocatalytically resolved to the corresponding enantiopure β-amino acids 7,9 with the aid of penicillin acylase (EC 3.5.1.11) from Escherichia coli. In substrates 6 the enantioselectivity of the biocatalytic process was practically uninfluenced by the nature of the fluoroalkyl chain. Thus, β-fluoroalkyl-β-alanines 7,9 bearing short (R = CF3, CHF2) or long [C3F7, H(CF2)4] chains were prepared in high enantiomeric parity. The (R)-enantiomer was the fast-reacting enantiomer in all cases.

    Original languageEnglish
    Pages (from-to)1119-1126
    Number of pages8
    JournalTetrahedron: Asymmetry
    Volume5
    Issue number6
    DOIs
    Publication statusPublished - Jun 1994

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