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


ALAGÖZ D., TÜKEL S. S. , YILDIRIM D.

APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, vol.177, no.6, pp.1348-1363, 2015 (Peer-Reviewed Journal) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 177 Issue: 6
  • Publication Date: 2015
  • Doi Number: 10.1007/s12010-015-1819-4
  • Journal Name: APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.1348-1363
  • Keywords: Prunus dulcis hydroxynitrile lyase, CLEA, Aromatic aldehydes and ketones, Enantiopure cyanohydrin, (R)-HYDROXYNITRILE LYASE, ENANTIOPURE CYANOHYDRINS, ASYMMETRIC-SYNTHESIS, GLUTARALDEHYDE, SEEDS, OPTIMIZATION, PURIFICATION, BIOCATALYSTS, STABILITY, PROTEINS

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 A degrees 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.