Bisepoxide Cross-Linked Enzyme Aggregates—New Immobilized Biocatalysts for Selective Biotransformations

Authors

  • Diána Weiser,

    1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3, H-1111 Budapest (Hungary), Fax: (+36) 1-463-3697
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  • Andrea Varga,

    1. Biocatalysis Research Group, Babeş-Bolyai University of Cluj-Napoca, Arany János str. 11, Ro-400028 Cluj-Napoca (Romania)
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  • Klaudia Kovács,

    1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3, H-1111 Budapest (Hungary), Fax: (+36) 1-463-3697
    2. Institute of Enzymology, Research Centre for Natural Sciences of Hungarian Academy of Sciences, Karolina út 29, H-1113 Budapest (Hungary)
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  • Flóra Nagy,

    1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3, H-1111 Budapest (Hungary), Fax: (+36) 1-463-3697
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  • Dr. András Szilágyi,

    1. Department of Physical Chemistry and Materials Science, Budapest University of Technology and Economics, Budafoki út 8, H-1111 Budapest (Hungary)
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  • Prof. Dr. Beáta G. Vértessy,

    1. Institute of Enzymology, Research Centre for Natural Sciences of Hungarian Academy of Sciences, Karolina út 29, H-1113 Budapest (Hungary)
    2. Department of Biotechnology and Food Sciences, Budapest University of Technology and Economics, Szt. Gellért tér 4, H-1111 Budapest (Hungary)
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  • Dr. Csaba Paizs,

    1. Biocatalysis Research Group, Babeş-Bolyai University of Cluj-Napoca, Arany János str. 11, Ro-400028 Cluj-Napoca (Romania)
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  • Prof. Dr. László Poppe

    Corresponding author
    1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3, H-1111 Budapest (Hungary), Fax: (+36) 1-463-3697
    2. SynBiocat Ltd, Lázár deák u 4/1, H-1173 Budapest (Hungary)
    • Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3, H-1111 Budapest (Hungary), Fax: (+36) 1-463-3697===

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Abstract

Glycerol diglycidyl ether (GDE) is a convenient and inexpensive bisepoxide cross-linker as demonstrated by the preparation of cross-linked enzyme aggregates (CLEAs) from two enzyme classes. The GDE CLEAs of lipase from Pseudomonas fluorescens (AK), lipase from Burkholderia cepacia (PS), and lipase B from Candida antarctica (CaL B) as well as of phenylalanine ammonia-lyase (PAL) from Petroselinum crispum demonstrated improved properties as compared with their glutaraldehyde (GA) cross-linked counterparts. Ultrasonication studies indicated that the GDE CLEAs of lipase PS and PAL were mechanically more stable than the GA CLEAs. In the kinetic resolution of rac-1-phenylethanol, the catalytic activity of the GDE–lipase CLEAs (U=69.6, 134.8, and 127.4 U g−1 for AK, CaL B, and PS prepared at 22 °C, respectively) surpassed that of the corresponding GA–lipase CLEAs (U=24.4, 131.0, and 119.2 U g−1 for AK, CaL B, and PS prepared at 22 °C, respectively). The GDE co-CLEAs from PAL and bovine serum albumin (BSA) could be recycled at least three times if used for the stereoselective ammonia addition in 6 M ammonia to (E)-3-(thiophen-2-yl)acrylic acid, whereas the recycling of the conventional GA–PAL CLEAs from this medium failed.

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