Electronic substituent effects in the nitrilase-catalyzed hydrolysis of para-substituted benzyl cyanides

Shimona Geresh, Yakir Giron, Ygal Gilboa, Robert Glaser

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

The initial rates of the nitrilase (Novo)-catalyzed hydrolysis of a series of para-substituted benzyl cyanides (R = NO2, Cl, OCH3, OH, NH2) were found to be susceptible to the nature of the para-substituent of the substrate and a Hammett-type linear free energy correlation was observed with ρ{variant} = 0.96. In a separate study, effective solubilization of substituted benzyl cyanide substrates having electron-donating groups (OH, NH2, OCH3) was achieved upon mixing with β-cyclodextrin to form 1:1 mol ratio inclusion complexes, but para-substituted benzyl cyanides with electron-withdrawing groups (Cl, NO2) were not fully solubilized under the same conditions. In addition, it was shown that the presence of β-cyclodextrin not only had no inhibitory effect on the enzyme activity, but it actually increased the initial rate of hydrolysis of the unsubstituted benzyl cyanide:β-cyclodextrin inclusion complex. However, the initial rates of hydrolysis were observed to be smaller when β-cyclodextrin was added to the para-substituted benzyl cyanides.

Original languageEnglish
Pages (from-to)10099-10102
Number of pages4
JournalTetrahedron
Volume49
Issue number44
DOIs
StatePublished - 1 Jan 1993

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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