Efficient kinetic resolution of organosilicon compounds by stereoselective esterification with hydrolases in organic solvent

Akinori Uejima, Toshiaki Fukui, Eiichiro Fukusaki, Tetsuo Omata, Takuo Kawamoto, Kenji Sonomoto, Atsuo Tanaka

Research output: Contribution to journalArticle

26 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)482-486
Number of pages5
JournalApplied Microbiology and Biotechnology
Volume38
Issue number4
DOIs
Publication statusPublished - Jan 1 1993

Fingerprint

Organosilicon Compounds
Esterification
Hydrolases
Silicon
Lipase
Carbon
Alcohols
Acids
Enzymes
2-trimethylsilyl-1-propanol

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Applied Microbiology and Biotechnology

Cite this

Efficient kinetic resolution of organosilicon compounds by stereoselective esterification with hydrolases in organic solvent. / Uejima, Akinori; Fukui, Toshiaki; Fukusaki, Eiichiro; Omata, Tetsuo; Kawamoto, Takuo; Sonomoto, Kenji; Tanaka, Atsuo.

In: Applied Microbiology and Biotechnology, Vol. 38, No. 4, 01.01.1993, p. 482-486.

Research output: Contribution to journalArticle

Uejima, Akinori ; Fukui, Toshiaki ; Fukusaki, Eiichiro ; Omata, Tetsuo ; Kawamoto, Takuo ; Sonomoto, Kenji ; Tanaka, Atsuo. / Efficient kinetic resolution of organosilicon compounds by stereoselective esterification with hydrolases in organic solvent. In: Applied Microbiology and Biotechnology. 1993 ; Vol. 38, No. 4. pp. 482-486.
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