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

    Research output: Contribution to journalArticlepeer-review

    77 Citations (Scopus)


    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 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
    Issue number6
    Publication statusPublished - Jun 1994


    Dive into the research topics of 'Biocatalytic resolution of β-fluoroalkyl-β-amino acids'. Together they form a unique fingerprint.

    Cite this