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Enantioselective Synthesis of Various Cyanohydrins Using Covalently Immobilized Preparations of Hydroxynitrile Lyase from Prunus dulcis

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Abstract

The carrier-based and carrier-free (cross-linked enzyme aggregate) covalent immobilizations of Prunus dulcis hydroxynitrile lyase were investigated. The immobilized preparations were tested for enantioselective carbon–carbon bond formation activity in the biphasic medium. Of the tested preparations, only cross-linked enzyme aggregate of P. dulcis hydroxynitrile lyase (PdHNL-CLEA) achieved the synthesis of (R)-mandelonitrile with 93 % yield and 99 % enantiopurity. PdHNL-CLEA was also used in the synthesis of various (R)-cyanohydrins from corresponding aldehydes/ketones and hydrocyanic acid. When 4-methoxybenzaldehyde, 4-methyl benzaldehyde, and 4-hydroxybenzaldehyde were used as substrates, the yield-enantiomeric excess of corresponding (R)-cyanohydrins were obtained as 95–95, 85–79, and 2–25 %, respectively, after 96 h at pH 4.0 and 5 °C. For acetophenone, 4-fluoroacetophenone, 4-chloroacetophenone, 4-bromoacetophenone, and 4-iodoacetophenone, the yield-enantiomeric excess of corresponding (R)-cyanohydrins were 1–99, 20–84, 11–95, 5–99, and 3–24 %, respectively at the same conditions. The results demonstrate PdHNL-CLEA can be effectively used in the synthesis of (R)-mandelonitrile.

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Acknowledgments

This study was financially supported by Cukurova University, Scientific Research Projects with the project number of IMYO2013BAP2.

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Authors and Affiliations

  1. Vocational School of Imamoglu, University of Cukurova, Adana, Turkey

    Dilek Alagöz

  2. Department of Chemistry, Faculty of Science and Letters, University of Cukurova, 01330, Adana, Turkey

    S. Seyhan Tükel

  3. Vocational School of Ceyhan, University of Cukurova, Adana, Turkey

    Deniz Yildirim

Authors
  1. Dilek Alagöz
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  2. S. Seyhan Tükel
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  3. Deniz Yildirim
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Correspondence to Dilek Alagöz.

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Alagöz, D., Tükel, S.S. & Yildirim, D. Enantioselective Synthesis of Various Cyanohydrins Using Covalently Immobilized Preparations of Hydroxynitrile Lyase from Prunus dulcis . Appl Biochem Biotechnol 177, 1348–1363 (2015). https://doi.org/10.1007/s12010-015-1819-4

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