Biotechnology Letters

, Volume 28, Issue 23, pp 1909–1912 | Cite as

Enzymatic synthesis of (R)-cyanohydrins by a novel (R)-oxynitrilase from Vicia sativa L.

Original Research Paper

Abstract

The defatted seed meal of common vetch (Vicia sativa L.) served as a source of (R)-oxynitrilase which catalyzed the enantioselective addition of HCN to aromatic, heteroaromatic, fluoro-substituted aromatic aldehydes to produce the corresponding enantiomeric pure cyanohydrins in yields of 52–100% and 88–99% ee at 12°C under micro-aqueous medium (diisopropyl ether) without addition of buffer solution.

Keywords

Biotransformation Common vetch Cyanohydrin Oxynitrilase Vicia sativa L. 

Notes

Acknowledgment

We are thankful to Nanjing University of Technology for financial support of this work.

References

  1. Chen P, Han S, Lin G, Huang H, Li Z (2001) A study of asymmetric hydrocyanation of heteroaryl carboxaldehydes catalyzed by (R)-oxynitrilase under micro-aqueous conditions. Tetrahedron: Asymmetry 12:3273–3279CrossRefGoogle Scholar
  2. De Gonzalo G, Brieva R, Gotor V (2002) (R)-Oxynitrilase-catalyzed transformation of ω-hydroxyalkanals. J Mol Catal B: Enzymatic 19–20: 223–230CrossRefGoogle Scholar
  3. Effenberger F, Forster S, Wajant H (2000) Hydroxynitrile lyase in stereoselective catalysis. Curr Opin Biotechnol 11:532–539PubMedCrossRefGoogle Scholar
  4. Garcia-Urdiales E, Alfonso I, Gotor V (2005) Enantioselective enzymatic desymmetrizations in organic synthesis. Chem Rev 105:313–354PubMedCrossRefGoogle Scholar
  5. Han S, Chen P, Lin G, Huang H, Li Z (2001) (R)-Oxynitrilase-catalyzed hydrocyanation: the first synthesis of optically active fluorinated mandelonitriles. Tetrahedron: Asymmetry 12:843–846CrossRefGoogle Scholar
  6. Han S, Lin G, Li Z (1998) Synthesis of (R)-cyanohydrins by crude (R)-oxynitrilase-catalyzed reactions in micro-aqueous medium. Tetrahedron: Asymmetry 9:1835–1838CrossRefGoogle Scholar
  7. Huang S, Liu S, Zong M, Xu R (2005) Synthesis of (R)-2-trimethylsilyl-2-hydroxyl-ethylcyanide catalyzed with (R)-oxynitrilase from loquat seed meal. Biotechnol Lett 27:79–82PubMedCrossRefGoogle Scholar
  8. Johnson D, Zabelinskaja-Mackova A, Griengl H (2000) Oxynitrilases for asymmetric C–C bond formation. Curr Opin Chem Biol 4:103PubMedCrossRefGoogle Scholar
  9. Jorns MS (1979) Mechanism of catalysis by the flavoenzyme oxynitrilase. J Biol Chem 254(23):12145–12152PubMedGoogle Scholar
  10. Nanda S, Kato Y, Asano Y (2005) A new (R)-hydroxynitrile lyase from Prunus mume: asymmetric synthesis of cyanohydrins. Tetrahedron 61:10908–10916CrossRefGoogle Scholar
  11. North M (2003) Synthesis and applications of non-racemic cyanohydrins. Tetrahedron: Asymmetry 14:147–176CrossRefGoogle Scholar
  12. Purkarthofer T, Gruber K, Fechter M, Griengl H (2005) Asymmetric biocatalytic hydrocyanation of pyrrole carboxaldehydes. Tetrahedron 61:7661–7668CrossRefGoogle Scholar
  13. Solis A, Luna H, Manjarrez N, Perez H (2004) Study on the (R)-oxynitrilase activity of Pouteria sapota. Tetrahedron 60:10427–10431CrossRefGoogle Scholar
  14. Solis A, Luna H, Perez H, Manjarrez N (2003) Evaluation of guanabana (Annona muricata) seed meal as a source of (S)-oxynitrilase. Tetrahedron: Asymmetry 14:2351–2353CrossRefGoogle Scholar
  15. Van Langen L, Selessa R, van Rantwijk F, Sheldon R (2005) Cross-linked aggregates of (R)-oxynitrilase: a stable, recyclable Biocatalyst for enantioselective hydrocyanation. Org Lett 7:327–329PubMedCrossRefGoogle Scholar
  16. Zandbergen P, van der Linden J, Brussee J, van der Gen A (1991) Synthesis of optically active cyanohydrins using almond meal. Synth Commun 21:1387–1391Google Scholar

Copyright information

© Springer Science+Business Media B.V. 2006

Authors and Affiliations

  • Shi-Qing Han
    • 1
  • Ping-Kai Ouyang
    • 1
  • Ping Wei
    • 1
  • Yi Hu
    • 1
  1. 1.College of Pharmacy and Life ScienceNanjing University of TechnologyNanjingChina

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