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. 1980 Jun;77(6):3095–3097. doi: 10.1073/pnas.77.6.3095

Benzoate catalysis in the hydrolysis of endo-5-[4′(5′)imidazolyl]-bicyclo[2.2.1]hept-endo- 2-yl trans-cinnamate: Implications for the charge-transfer mechanism of catalysis by serine proteases

John D Roberts 1, Keiko Kanamori 1
PMCID: PMC349558  PMID: 16592829

Abstract

The acceleration, by a factor of 2500, of the hydrolysis of endo-5-[4′(5′)imidazolyl]bicyclo[2.2.1]hept-endo- 2-yl trans-cinnamate by 0.5 M sodium benzoate in 42 mol% dioxane in water can be explained without resort to operation of a “charge-relay” mechanism similar to that often postulated to account for the enzymatic activity of serine proteases. The degree of ionization of 4-methylimidazole and of sodium benzoate in 42 mol% dioxane in water at 60°C have been measured by NMR spectroscopy.

Keywords: 13C and 15N NMR spectroscopy, ester hydrolysis, base catalysis, medium effects on reaction rates, enzyme mechanisms

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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