Selectivity of the (S)-oxynitrilase from Hevea brasiliensis towards α- and β-substituted aldehydes

Gabriella Roda, Sergio Riva, Bruno Danieli, Herfried Griengl, Uwe Rinner, Michael Schmidt, Antonina Mackova Zabelinskaja

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The performance of (S)-oxynitrilase from Hevea brasiliensis (HbHNL) has been investigated with several α- and β-substituted alkyl or alkoxy aldehydes and the results have been compared to the data previously obtained with the (R)-specific enzyme from almonds (PaHNL). With both enzymes there was no chiral discrimination between the enantiomers of the racemic substrates, therefore this reaction cannot be used as a preparative method to achieve both the kinetic resolution of the starting racemic aldehyde and the production of diastereomerically pure (or enriched) cyanohydrins. Additionally, in comparison with the (R)-PaHNL the (S)-selective enzyme from Hevea gave products with higher de, but was more negatively effected by oxygenated substituents.

Original languageEnglish
Pages (from-to)2979-2983
Number of pages5
JournalTetrahedron
Volume58
Issue number15
DOIs
Publication statusPublished - Apr 8 2002

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mandelonitrile lyase
Hevea
Aldehydes
Enzymes
Enantiomers
Kinetics
Substrates

Keywords

  • Cyanohydrins
  • Hevea brasiliensis
  • Oxynitrilases
  • Prunus amygdalus
  • Substituted aldehydes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Roda, G., Riva, S., Danieli, B., Griengl, H., Rinner, U., Schmidt, M., & Mackova Zabelinskaja, A. (2002). Selectivity of the (S)-oxynitrilase from Hevea brasiliensis towards α- and β-substituted aldehydes. Tetrahedron, 58(15), 2979-2983. https://doi.org/10.1016/S0040-4020(02)00187-4

Selectivity of the (S)-oxynitrilase from Hevea brasiliensis towards α- and β-substituted aldehydes. / Roda, Gabriella; Riva, Sergio; Danieli, Bruno; Griengl, Herfried; Rinner, Uwe; Schmidt, Michael; Mackova Zabelinskaja, Antonina.

In: Tetrahedron, Vol. 58, No. 15, 08.04.2002, p. 2979-2983.

Research output: Contribution to journalArticle

Roda, G, Riva, S, Danieli, B, Griengl, H, Rinner, U, Schmidt, M & Mackova Zabelinskaja, A 2002, 'Selectivity of the (S)-oxynitrilase from Hevea brasiliensis towards α- and β-substituted aldehydes', Tetrahedron, vol. 58, no. 15, pp. 2979-2983. https://doi.org/10.1016/S0040-4020(02)00187-4
Roda, Gabriella ; Riva, Sergio ; Danieli, Bruno ; Griengl, Herfried ; Rinner, Uwe ; Schmidt, Michael ; Mackova Zabelinskaja, Antonina. / Selectivity of the (S)-oxynitrilase from Hevea brasiliensis towards α- and β-substituted aldehydes. In: Tetrahedron. 2002 ; Vol. 58, No. 15. pp. 2979-2983.
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