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Bioorg Med Chem. 2010 Sep 15;18(18):6651-6. doi: 10.1016/j.bmc.2010.07.070. Epub 2010 Aug 6.

Chiral switch of enzymatic ketone reduction by addition of gamma-cyclodextrin.

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  • 1Department of Analytical Chemistry, Institute of Chemical Technology Prague, Technicka 5, 166 28 Prague 6-Dejvice, Czech Republic.


We report a chiral switch in the configuration of 1-(p-methoxyphenyl)-propan-2-ol, synthesized in aqueous media by ketoreductase in the presence of high concentration of gamma-CD. NMR, ECD and fluorescence spectrometry were used in the effort to explain this unexpected effect. A comparison has been made between the catalytic activity of the enzyme and alpha-helix content in the conformation and it has been observed that enzyme is most active at the maximum alpha-helix content. The beta-sheet content and random coil conformation in the enzyme were found to be dependent on cyclodextrin concentration.

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