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Updated: Feb 18, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Development of Spiroligomer-Peptoid Hybrids.

Justin D Northrup¹, Giulia Mancini², Claire R Purcell¹

¹Department of Chemistry, Temple University , Philadelphia, Pennsylvania 19122, United States.

The Journal of Organic Chemistry

|November 22, 2017

Summary

Researchers developed novel spiroligomer-peptoid hybrids by preorganizing functional groups in 3D space. This approach enhances molecular diversity and facilitates protein interactions, offering new possibilities for ligand discovery.

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Last Updated: Feb 18, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Solid-phase Submonomer Synthesis of Peptoid Polymers and their Self-Assembly into Highly-Ordered Nanosheets

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Published on: November 2, 2011

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

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

Published on: June 20, 2014

Area of Science:

Chemical Synthesis
Macromolecular Chemistry
Drug Discovery

Background:

Proteins exhibit remarkable functional diversity due to their complex structures.
Peptoids are versatile molecules known to interact with proteins and aid in ligand discovery.
Developing synthetic macromolecules with protein-like functionality remains a significant challenge.

Purpose of the Study:

To create novel spiroligomer-peptoid hybrids with preorganized functional groups.
To enhance stereochemical diversity and reduce conformational flexibility in synthetic molecules.
To explore new avenues for designing ligands with improved protein-binding capabilities.

Main Methods:

Synthesis of 15 new spiroligomer monomer amines with two stereocenters and three functional groups.
Synthesis of a spiroligomer trimer with six stereocenters and five functional groups.
Utilizing these novel amines to construct five first-generation spiroligomer-peptoid hybrids.

Main Results:

Successfully synthesized 15 spiroligomer monomer amines and one spiroligomer trimer.
Achieved high yields (67-84%) for the monomer amines from a common hydantoin precursor.
Created five distinct spiroligomer-peptoid hybrids, demonstrating the feasibility of the approach.

Conclusions:

Spiroligomer-peptoid hybrids offer a promising strategy for creating functional macromolecules.
The spirocyclic core effectively preorganizes functional groups, increasing stereochemical diversity.
This platform holds potential for the discovery of novel protein-binding ligands.