Separation of electronic and hydrophobic effects for the papain hydrolysis of substituted N-benzoylglycine esters

Add time:07/18/2019    Source:sciencedirect.com

The role of hydrophobic and electronic effects on the kinetic constants kcat and Km for the papain hydrolysis of a series of 22 substituted N-benzoylglycine pyridyl esters was investigated. The series studied comprises a wide variety of substituents on the N-benzoyl ring, with about a 300 000-fold range in their hydrophobicities, and 2.1-fold range in their electronic Hammet constants(σ). It was found that the variation in the log kcat and log 1/Km constants could be explained by the following quantitative-structure activity relationships (QSAR): log1/Km= 0.40 π4 + 4.40 and log1/kcat= 0.45 σ + 0.18. The substituent constant, π4, is the hydrophobic parameter for the 4-N-benzoyl substituents. QSAR analysis of two smaller sets of glycine phenyl and methyl esters produced similar results. A clear separation of the substituent effects indicates that in the case of these particular esters, acylation appears to be the rate limiting catalytic step.

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