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Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library

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Universal peptidomimetics.

Eunhwa Ko¹, Jing Liu, Lisa M Perez

¹Department of Chemistry and Laboratory for Molecular Simulation, Texas A&M University, Box 30012, College Station, Texas 77842, United States.

Journal of the American Chemical Society

|December 25, 2010

Summary

This summary is machine-generated.

This study introduces minimalist mimics, novel peptidomimetic scaffolds designed to mimic amino acid side chains in protein secondary structures. These universal peptidomimetics are valuable for high-throughput screening library design.

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Published on: November 2, 2011

Area of Science:

Medicinal Chemistry
Organic Chemistry
Computational Chemistry

Background:

Peptidomimetics aim to replicate peptide structures and functions.
Mimicking amino acid side chains in secondary structures is challenging due to conformational penalties.

Purpose of the Study:

To design universal peptidomimetic scaffolds capable of mimicking local amino acid pairs in any secondary structure.
To develop minimalist mimics with reduced entropic and enthalpic penalties.

Main Methods:

Design of four novel peptidomimetic scaffolds.
Synthesis of compound libraries with diverse amino acid side chains.
Computational modeling to assess conformational accessibilities.

Main Results:

Peptidomimetics based on the four scaffolds can adopt conformations mimicking various local amino acid side chain combinations.
These scaffolds effectively present side chains in conformations resembling those in protein secondary structures.
Demonstrated utility for high-throughput screening library design.

Conclusions:

The developed minimalist mimics represent a universal peptidomimetic strategy.
These scaffolds are suitable for generating diverse libraries for drug discovery.
Data from submission to the NIH Molecular Libraries Small Molecule Repository (MLSMR) are presented.