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Deciphering the Structural Effects of Activating EGFR Somatic Mutations with Molecular Dynamics Simulation

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Fluorogenic structure activity library pinpoints molecular variations in substrate specificity of structurally

Alex White¹, Andrew Koelper¹, Arielle Russell¹

¹From the Department of Chemistry and Biochemistry, Butler University, Indianapolis, Indiana 46208-3443 and.

The Journal of Biological Chemistry

|July 15, 2018

Summary

Cellular esterases

Keywords:

carboxylesterase chemical biology chemical probes fluorescence fluorogenic substrates hydrolase serine hydrolase structure-activity relationship substrate specificity

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Published on: November 3, 2011

Area of Science:

Biochemistry and enzymology
Molecular biology
Structural biology

Background:

Cellular esterases perform vital biological functions through substrate hydrolysis.
Esterase promiscuity complicates the determination of substrate preferences and functions.
Understanding esterase substrate recognition is crucial for various biological and biotechnological applications.

Purpose of the Study:

To identify universal factors governing esterase substrate recognition.
To systematically interrogate esterase preferences for substrate features like chain length, branching, and polarity.
To differentiate common classes of esterase substrates and refine specificity of homologous enzymes.

Main Methods:

Design and synthesis of a 32-member structure-activity relationship (SAR) library of fluorogenic ester substrates.
Screening of two structurally homologous bacterial esterases (Vibrio cholerae ybfF and Mycobacterium tuberculosis Rv0045c) against the substrate library.
Site-directed mutagenesis to investigate the role of specific residues (Tyr-119 and His-187) in substrate selectivity.

Main Results:

Refined substrate specificities for two homologous bacterial esterases, differentiating their preferences.
Vibrio cholerae esterase ybfF showed preference for γ-position thioethers and ethers.
Rv0045c from Mycobacterium tuberculosis preferred branched substrates, with or without thioethers.
Individual selectivity residues (Tyr-119 in ybfF, His-187 in Rv0045c) were identified as key controllers of substrate preference, with reciprocal substitutions altering specificity.

Conclusions:

Esterase selectivity is tuned by transition state stabilization.
Thioethers represent an underutilized functional group for designing esterase substrates.
A rapid method for differentiating structural isozymes was developed, with potential applications in imaging, biocatalyst screening, and inhibitor design.