Abstract
The cleavage of mandelonitrile catalysed by hydroxynitrile lyases (HNL) from Prunus amygdalus (PaHNL) and Manihot esculenta (MeHNL) proceeded more rapidly in monophasic aqueous media containing 1-propyl-3-methylimidazolium tetrafluoroborate [C4MIm][BF4] than in media containing acetonitrile or THF. Both HNLs were much more thermostable in [C4MIm][BF4] than in acetonitrile or THF. The addition of each of the four ionic liquids 1-butyl-, 1-pentyl- and 1-hexyl-3-methylimidazolium tetrafluoroborates at 2–6% (v/v in the aqueous phase) increased both the enzyme activity and the product e.e. in the PaHNL-catalysed transcyanation in an aqueous/DIPE biphasic system. However, MeHNL was inactivated by the ionic liquids, as indicated by the decreased reaction rate, substrate conversion and product e.e.
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References
RP Gaisberger MH Fechter H Griengl (2004) ArticleTitleThe first hydroxynitrile lyase catalysed cyanohydrin formation in ionic liquids Tetrahedron: Asymmetry 15 2959–2963 Occurrence Handle10.1016/j.tetasy.2004.06.028
RJH Gregory (1999) ArticleTitleCyanohydrins in nature and the laboratory: biology, preparations, and synthetic applications Chem. Rev. 99 3649–3682 Occurrence Handle10.1021/cr9902906 Occurrence Handle11849033
U Kragl M Eckstein N Kaftzik (2002) ArticleTitleEnzyme catalysis in ionic liquids Curr. Opin. Biotechnol. 13 565–571 Occurrence Handle10.1016/S0958-1669(02)00353-1 Occurrence Handle12482515
N Li MH Zong C Liu HS Peng H-C Wu (2003) ArticleTitle(R)-oxynitrilase-catalysed synthesis of chiral silicon-containing aliphatic (R)-ketone-cyanohydrins Biotechnol. Lett. 25 219–222 Occurrence Handle10.1023/A:1022316919552 Occurrence Handle12882574
S Park RJ Kazlauskas (2001) ArticleTitleImproved preparation and use of room-temperature ionic liquids in lipase-catalyzed enantio- and regioselective acylations J. Org. Chem. 66 8395–8401 Occurrence Handle10.1021/jo015761e Occurrence Handle11735517
RA Sheldon RM Lau MJ Sorgedrager F Rantwijk Particlevan KR Seddon (2002) ArticleTitleBiocatalysis in ionic liquids Green Chem. 4 147–151 Occurrence Handle10.1039/b110008b
T Welton (1999) ArticleTitleRoom-temperature ionic liquids: solvents for synthesis and catalysis Chem. Rev. 99 2071–2083 Occurrence Handle10.1021/cr980032t Occurrence Handle11849019
R Xu MH Zong YY Liu J He YY Zhang WY Lou (2004) ArticleTitleEnzymatic enantioselective transcyanation of silicon-containing aliphatic ketone with (S)-hydroxynitrile lyase from Manihot esculenta Appl. Microbiol. Biotechnol. 66 IssueID1 27–33 Occurrence Handle10.1007/s00253-004-1708-1 Occurrence Handle15309340
H Zhao SV Malhotra (2002) ArticleTitleEnzymatic resolution of amino acid esters using ionic liquid N-ethyl pyridinium trifluoroacetate Biotechnol. Lett. 24 1257–1260 Occurrence Handle10.1023/A:1016205924504
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Lou, WY., Xu, R. & Zong, MH. Hydroxynitrile Lyase Catalysis in Ionic Liquid-containing Systems. Biotechnol Lett 27, 1387–1390 (2005). https://doi.org/10.1007/s10529-005-0686-4
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DOI: https://doi.org/10.1007/s10529-005-0686-4