Preparation of optically active 1-aminoalkylphosphonic acids by stereoselective enzymatic hydrolysis of racemic N-acylated 1-aminoalkylphosphonic acids

V. A. Solodenko, T. N. Kasheva, V. P. Kukhar, E. V. Kozlova, D. A. Mironenko, V. K. Švedas

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    47 Citations (Scopus)

    Abstract

    N-Phenylacetylated derivatives of 1-aminoalkylphosphonic acids were synthesized and high enantioselectivity of their hydrolysis by penicillin acylase (EC 3.5.1.11) was demonstrated. Stereoselective enzymatic hydrolysis of racemic 1-(N-phenylacetylamino)alkylphosphonic acids was used for preparation of enantiomeric 1-aminoalkylphosphonic acids. The kinetic regularities of penicillin acylase catalyzed hydrolysis were established and the biocatalytic process was optimized to increase the optical purity and the yield of the optically active product.

    Original languageEnglish
    Pages (from-to)3989-3998
    Number of pages10
    JournalTetrahedron
    Volume47
    Issue number24
    DOIs
    Publication statusPublished - 1991

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