Abstract
Stereoselective esterification of three isomers of trimethylsilylpropanol, 1-trimethylsilyl-2-propanol, 1-trimethylsilyl-1-propanol, and 2-trimethylsilyl-1-propanol, was systematically studied with five kinds of hydrolases in an organic solvent system in connection with the structure of the compounds. The hydrolases were found to be able to esterify these organosilicon compounds, even β-hydroxyalkylsilanes, which are unstable under the conditions of acid-catalysed esterification, and the highly optically active organosilicon compounds were successfully prepared with the selected hydrolases. Even a primary alcohol, 2-trimethylsilyl-1-propanol, was stereoselectively esterified by lipase. Furthermore, comparative studies were made by using their carbon counterparts. The silicon atom in the substrates was found to enhance the enzyme stereoselectivity in some cases, but its effect on the substrate reactivity was dependent on the structure of the substrates. These results are discussed based on the specific characters of the silicon atom.
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Correspondence to: A. Tanaka
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Uejima, A., Fukui, T., Fukusaki, E. et al. Efficient kinetic resolution of organosilicon compounds by stereoselective esterification with hydrolases in organic solvent. Appl Microbiol Biotechnol 38, 482–486 (1993). https://doi.org/10.1007/BF00242942
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DOI: https://doi.org/10.1007/BF00242942