Enzymatic conversion of artificial organosilicon compounds by alcohol dehydrogenase

K. Sonomoto, H. Oiki, Y. Kato

研究成果: ジャーナルへの寄稿記事

4 引用 (Scopus)

抄録

Among the commercially available alcohol dehydrogenases from different sources tested, equine liver alcohol dehydrogenase (HLADH) recognized several organosilicon compounds, sila-substituted alcohols, as substrates and exhibited oxidative activity. Especially large differences in catalytic rates were observed between trimethylsilyl alcohols [Me3Si(CH2)nOH] but not between the carbon analogues. Thus, the activity of HLADH was extremely and peculiarly affected by the trimethylsilyl group in the organosilicon compounds [trimethylsilylmethanol (n = 1), 27%; trimethylsilylethanol (n = 2), 212%; trimethylsilylpropanol (n = 3), 65%; ethanol, 100%]. These differences might result from the β-effect of the trimethylsilyl group (stabilization of a negative charge on the carbon α to the silicon and a positive charge on the carbon β to the silicon) by considering the possible mechanisms for hydrogen transfer at the HLADH active site. As a result of kinetic investigations with HLADH, trimethylsilylethanol was found to show high affinity compared with the others. Furthermore, enhancement of HLADH activity derived from sila-substitution was not easily provided even by the use of the corresponding carbon analogues with electron attractive groups (for example, 3-methoxy-3-methylbutanol).

元の言語英語
ページ(範囲)640-643
ページ数4
ジャーナルEnzyme and Microbial Technology
14
発行部数8
DOI
出版物ステータス出版済み - 8 1992

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Organosilicon Compounds
Alcohol Dehydrogenase
Alcohols
Carbon
Silicon
Pentanols
Liver
Horses
Hydrogen
Catalytic Domain
Ethanol
Substitution reactions
Stabilization
Electrons
Kinetics
Oxidoreductases
Substrates

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Bioengineering
  • Biochemistry
  • Applied Microbiology and Biotechnology

これを引用

Enzymatic conversion of artificial organosilicon compounds by alcohol dehydrogenase. / Sonomoto, K.; Oiki, H.; Kato, Y.

:: Enzyme and Microbial Technology, 巻 14, 番号 8, 08.1992, p. 640-643.

研究成果: ジャーナルへの寄稿記事

Sonomoto, K. ; Oiki, H. ; Kato, Y. / Enzymatic conversion of artificial organosilicon compounds by alcohol dehydrogenase. :: Enzyme and Microbial Technology. 1992 ; 巻 14, 番号 8. pp. 640-643.
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