Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 18, Issue 18, Pages 6651-6656Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2010.07.070
Keywords
Enzymatic reduction; Cyclodextrins; Chiral switch; Spectroscopy
Funding
- Ministry of Education of the Czech Republic [MSM6036137307, LC06077, LC512]
- Grant Agency of the Czech Republic [P301/10/1426]
- Grant Agency of the Academy of Sciences of the Czech Republic [KAN200200651]
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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. (c) 2010 Elsevier Ltd. All rights reserved.
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