Enzymatic conversion of artificial organosilicon compounds by alcohol dehydrogenase

Kenji Sonomoto, H. Oiki, Y. Kato

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)640-643
Number of pages4
JournalEnzyme and Microbial Technology
Volume14
Issue number8
DOIs
Publication statusPublished - Jan 1 1992
Externally publishedYes

Fingerprint

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

Cite this

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

In: Enzyme and Microbial Technology, Vol. 14, No. 8, 01.01.1992, p. 640-643.

Research output: Contribution to journalArticle

Sonomoto, Kenji ; Oiki, H. ; Kato, Y. / Enzymatic conversion of artificial organosilicon compounds by alcohol dehydrogenase. In: Enzyme and Microbial Technology. 1992 ; Vol. 14, No. 8. pp. 640-643.
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