Biotechnology Letters

, Volume 27, Issue 2, pp 79–82 | Cite as

Synthesis of (R)-2-trimethylsilyl-2-hydroxyl-ethylcyanide catalyzed with (R)-oxynitrilase from loquat seed meal

  • Shun-Rong Huang
  • Sen-Lin Liu
  • Min-Hua Zong
  • Ruo Xu


The synthesis of optically active (R)-2-trimethylsilyl-2-hydroxyl-ethylcyanide by asymmetric trans-cyanation of acetyltrimethylsilane with acetone cyanohydrin in a biphasic system was achieved using (R)-oxynitrilase from loquat seed meal. Diisopropyl ether was the most suitable organic phase among the organic solvents examined. The optimal concentration of acetyltrimethylsilane, concentration of crude enzyme, volume ratio of the aqueous to the organic phase, temperature and the buffer pH value were 14 mM, 61.4 U ml-1, 13% (v/v), 30 °C and 4, respectively. The substrate conversion and the product enantiomeric excess were 95% and 98% under the optimized conditions. Acetyltrimethylsilane was a better substrate of the enzyme than its carbon counterpart.


cyanohydrin organosilicon compound (R)-oxynitrilase transcyanation (R)-2-trimethylsilyl- 2-hydroxyl-ethylcyanide 


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  1. Bains, W, Tacke, R 2003Silicon chemistry as a novel source of chemical diversity in drug designCurr. Opin. Drug Discov. Devel.6526543Google Scholar
  2. Costes, D, Wehtje, E, Adlercreutz, P 2001Cross-linked crystals of hydroxynitrile lyase as catalyst for the synthesis of optically active cyanohydrinsJ. Mol. Catal. B: Enzymatic11607612Google Scholar
  3. Effenberger, F, Heid, S 1995(R)-Oxynitrilase catalyzed synthesis of (R)-ketone cyanohydrinsTetrahedr.: Asymmetry629452952Google Scholar
  4. Gerrits, PJ, Willeman, WF, Straathof, AJJ, Heijnen, JJ, Brussee, J, van der Gen, A 2001Mass transfer limitation as a tool to enhance the enantiomeric excess in the enzymatic synthesis of chiral cyanohydrinsJ. Mol. Catal. B: Enzymatic15111121Google Scholar
  5. Gregory, RJH 1999Cyanohydrins in nature and the laboratory: biology, preparations, and synthetic applicationsChem. Rev.9936493682Google Scholar
  6. Griengl, H, Klempier, N, Pochlauer, P, Schmidt, M, Shi, NY, Zabelinskaja-Mackova, AA 1998Enzyme catalysed formation of (S)-cyanohydrins derived from aldehydes and ketones in a biphasic solvent systemTetrahedron541447714486Google Scholar
  7. Han, SQ, Chen, PR, Lin, GQ, Huang, H, Li, ZY 2001(R)-oxynitrilase-catalyzed hydrocyanation: the first synthesis of optically active fluorinated mandelonitrilesTetrahedr.: Asymmetry12843846Google Scholar
  8. Kawamoto, T, Yamanaka, H, Tanaka, A 2000Enzymatic preparation of optically active silicon-containing amino acids and their applicationAppl. Biochem. Biotech.881722Google Scholar
  9. Kiljunen, E, Kanerva, LT 1996(R)- and (S)-Cyanohydrins using oxynitrilases in whole cellsTetrahedr.: Asymmetry711051116Google Scholar
  10. Li, N, Zong, MH, Liu, C, Peng, HS, Wu, HC 2003a(R)-Oxynitrilase-catalysed synthesis of chiral silicon-containing aliphatic (R)-ketone-cyanohydrinsBiotechnol. Lett.25219222Google Scholar
  11. Li, N, Zong, MH, Peng, HS, Wu, HC, Liu, C 2003b(R)-Oxynitrilase-catalyzed synthesis of (R)-2-trimethylsilyl-2-hydroxyl-ethylcyanideJ. Mol. Catal. B: Enzymatic22712Google Scholar
  12. Smith, RJ, Pietzsch, M, Waniek, T, Syldatk, C, Bienz, S 2001Enzymatic synthesis of enantiomerically enriched d- and l-3-silylated alanines by deracemization of dl-5-silylmethylated hydantoinsTetrahedr.: Asymmetry12157165Google Scholar
  13. Willeman, WF, Straathof, AJJ, Heijnen, JJ 2002Reaction temperature optimization procedure for the synthesis of (R)-mandelonitrile by Prunus amygdalus hydroxynitrile lyase using a process model approachEnzyme Microb. Technol.30200208Google Scholar
  14. Zani, P 2001Biotransformations of organosilicon compounds: enantioselective reduction of acyl silanes by means of baker’s yeastJ. Mol. Catal. B: Enzymatic11279285Google Scholar

Copyright information

© Springer 2005

Authors and Affiliations

  • Shun-Rong Huang
    • 1
  • Sen-Lin Liu
    • 2
  • Min-Hua Zong
    • 1
  • Ruo Xu
    • 1
  1. 1.Department of BiotechnologySouth China University of TechnologyGuangzhouP.R. China
  2. 2.College of Life ScienceShenzhen UniversityShenzhenP.R. China

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