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Title: Submonomer synthesis of sequence defined peptoids with diverse side-chains.

Abstract

Peptoids are a diverse family of sequence-defined oligomers of N-substituted glycine monomers, that can be readily accessed by the solid-phase submonomer synthesis method. Due to the versatility and efficiency of this chemistry, and the easy access to hundreds of potential monomers, there is an enormous potential sequence space that can be explored. This has enabled researchers from many different fields to custom-design peptoid sequences tailored to a wide variety of problems in biomedicine, nanoscience and polymer science. Here we provide detailed protocols for the synthesis of peptoids, using optimized protocols that can be performed by non-chemists. The submonomer method is fully compatible with Fmoc-peptide synthesis conditions, so the method is readily automated on existing automated peptide synthesizers using protocols provided here. Although the submonomer synthesis for peptoids is well established, there are special considerations required in order to access many of the most useful and desirable sidechains. Here we provide methods to include most of the amino-acid-like side chains, some of the most important non-natural monomer classes, as well as the creation of peptoid conjugates and peptide-peptoid hybrids.

Authors:
; ; ;
Publication Date:
Research Org.:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1845665
DOE Contract Number:  
AC02-05CH11231
Resource Type:
Book
Resource Relation:
Related Information: Book Title: Methods in Enzymology
Country of Publication:
United States
Language:
English

Citation Formats

Connolly, Michael D, Xuan, Sunting, Molchanova, Natalia, and Zuckermann, Ronald N. Submonomer synthesis of sequence defined peptoids with diverse side-chains.. United States: N. p., 2021. Web. doi:10.1016/bs.mie.2021.04.022.
Connolly, Michael D, Xuan, Sunting, Molchanova, Natalia, & Zuckermann, Ronald N. Submonomer synthesis of sequence defined peptoids with diverse side-chains.. United States. https://doi.org/10.1016/bs.mie.2021.04.022
Connolly, Michael D, Xuan, Sunting, Molchanova, Natalia, and Zuckermann, Ronald N. 2021. "Submonomer synthesis of sequence defined peptoids with diverse side-chains.". United States. https://doi.org/10.1016/bs.mie.2021.04.022. https://www.osti.gov/servlets/purl/1845665.
@article{osti_1845665,
title = {Submonomer synthesis of sequence defined peptoids with diverse side-chains.},
author = {Connolly, Michael D and Xuan, Sunting and Molchanova, Natalia and Zuckermann, Ronald N},
abstractNote = {Peptoids are a diverse family of sequence-defined oligomers of N-substituted glycine monomers, that can be readily accessed by the solid-phase submonomer synthesis method. Due to the versatility and efficiency of this chemistry, and the easy access to hundreds of potential monomers, there is an enormous potential sequence space that can be explored. This has enabled researchers from many different fields to custom-design peptoid sequences tailored to a wide variety of problems in biomedicine, nanoscience and polymer science. Here we provide detailed protocols for the synthesis of peptoids, using optimized protocols that can be performed by non-chemists. The submonomer method is fully compatible with Fmoc-peptide synthesis conditions, so the method is readily automated on existing automated peptide synthesizers using protocols provided here. Although the submonomer synthesis for peptoids is well established, there are special considerations required in order to access many of the most useful and desirable sidechains. Here we provide methods to include most of the amino-acid-like side chains, some of the most important non-natural monomer classes, as well as the creation of peptoid conjugates and peptide-peptoid hybrids.},
doi = {10.1016/bs.mie.2021.04.022},
url = {https://www.osti.gov/biblio/1845665}, journal = {},
number = ,
volume = ,
place = {United States},
year = {Fri Jan 01 00:00:00 EST 2021},
month = {Fri Jan 01 00:00:00 EST 2021}
}

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Works referenced in this record:

Isolation of Protein Ligands from Large Peptoid Libraries
journal, October 2003


The Role of Hydrogen Bonding in Peptoid-Based Marine Antifouling Coatings
journal, January 2019


A practical method for the synthesis of peptoids containing both lysine-type and arginine-type monomers
journal, January 2016


Incorporation of Unprotected Heterocyclic Side Chains into Peptoid Oligomers via Solid-Phase Submonomer Synthesis
journal, July 2003


Peptoid ligands that bind selectively to phosphoproteins
journal, September 2011


The Click Triazolium Peptoid Side Chain: A Strong cis -Amide Inducer Enabling Chemical Diversity
journal, May 2012


Polypeptoid polymers: Synthesis, characterization, and properties
journal, October 2017


Short Alkylated Peptoid Mimics of Antimicrobial Lipopeptides
journal, October 2010


A Peptoid Ribbon Secondary Structure
journal, April 2013


Peptoids as tools and sensors
journal, April 2019


Solid-Phase Synthesis of N-Substituted Glycine Oligomers (α‑Peptoids) and Derivatives
journal, August 2010


In Vivo, In Vitro, and In Silico Characterization of Peptoids as Antimicrobial Agents
journal, February 2016


Conformations of peptoids in nanosheets result from the interplay of backbone energetics and intermolecular interactions
journal, May 2018


Investigating the Anti-leishmanial Effects of Linear Peptoids
journal, December 2014


[25] Synthesis of N-substituted glycine peptoid libraries
book, January 1996


New Strategies for the Design of Folded Peptoids Revealed by a Survey of Noncovalent Interactions in Model Systems
journal, November 2009


A Peptoid Square Helix via Synergistic Control of Backbone Dihedral Angles
journal, June 2017


Liquid-Crystalline Phase Behavior in Polypeptoid Diblock Copolymers
journal, November 2018


Universal Relationship between Molecular Structure and Crystal Structure in Peptoid Polymers and Prevalence of the cis Backbone Conformation
journal, January 2018


Clickity-click: highly functionalized peptoid oligomers generated by sequential conjugation reactions on solid-phase support
journal, January 2006


Development of homomultimers and heteromultimers of lung cancer-specific peptoids
journal, January 2011


Enhanced detection of prion infectivity from blood by preanalytical enrichment with peptoid-conjugated beads
journal, September 2019


Learning from Host-Defense Peptides: Cationic, Amphipathic Peptoids with Potent Anticancer Activity
journal, February 2014


Highly stable and self-repairing membrane-mimetic 2D nanomaterials assembled from lipid-like peptoids
journal, July 2016


Designable and dynamic single-walled stiff nanotubes assembled from sequence-defined peptoids
journal, January 2018


Precisely tuneable energy transfer system using peptoid helix-based molecular scaffold
journal, July 2017


Ultra-Short Antimicrobial Peptoids Show Propensity for Membrane Activity Against Multi-Drug Resistant Mycobacterium tuberculosis
journal, March 2020


Unusual truncation of N-acylated peptoids under acidic conditions
journal, January 2014


A cleavage method which minimizes side reactions following Fmoc solid phase peptide synthesis
journal, September 1990


A modular platform to develop peptoid-based selective fluorescent metal sensors
journal, January 2017


A Peptoid-Based Fluorescent Sensor for Cyanide Detection
journal, March 2016


Unbiased Selection of Peptide–Peptoid Hybrids Specific for Lung Cancer Compared to Normal Lung Epithelial Cells
journal, October 2015


Unnatural amino acids improve affinity and modulate immunogenicity: Developing peptides to treat MHC type II autoimmune disorders
journal, March 2018


Advances in Development of Antimicrobial Peptidomimetics as Potential Drugs
journal, August 2017


Hierarchical Self-Assembly of a Biomimetic Diblock Copolypeptoid into Homochiral Superhelices
journal, November 2010


Peptoid-Peptide Hybrid Backbone Architectures
journal, December 2009


Peptomers: A Versatile Approach for the Preparation of Diverse Combinatorial Peptidomimetic Bead Libraries
journal, March 1997


A Readily Applicable Strategy to Convert Peptides to Peptoid-based Therapeutics
journal, March 2013


N -Naphthyl Peptoid Foldamers Exhibiting Atropisomerism
journal, January 2012


Accelerated Submonomer Solid-Phase Synthesis of Peptoids Incorporating Multiple Substituted N -Aryl Glycine Monomers
journal, August 2015


Mass spectrometry studies of the fragmentation patterns and mechanisms of protonated peptoids
journal, June 2020


Design, Synthesis, Assembly, and Engineering of Peptoid Nanosheets
journal, January 2016


The tert -Butyl Side Chain: A Powerful Means to Lock Peptoid Amide Bonds in the Cis Conformation
journal, April 2013


Strengthening Peptoid Helicity through Sequence Site-Specific Positioning of Amide cis -Inducing Nt Bu Monomers
journal, December 2019


Extreme stability of helices formed by water-soluble poly-N-substituted glycines (polypeptoids) with ?-chiral side chains
journal, December 2001


Cation-Induced Molecular Switching Based on Reversible Modulation of Peptoid Conformational States
journal, September 2018


Design of Peptoid-peptide Macrocycles to Inhibit the β-catenin TCF Interaction in Prostate Cancer
journal, October 2018


Poly(α-Peptoid)s Revisited: Synthesis, Properties, and Use as Biomaterial: Poly(α-Peptoid)s Revisited: Synthesis, Properties, and Use
journal, April 2015


Conformational Rearrangements by Water-Soluble Peptoid Foldamers
journal, October 2007


Peptoids: a modular approach to drug discovery.
journal, October 1992


Stereochemistry of polypeptoid chain configurations
journal, March 2019


Toward a clinical antifungal peptoid: Investigations into the therapeutic potential of AEC5
journal, April 2019


Solution Self-Assemblies of Sequence-Defined Ionic Peptoid Block Copolymers
journal, February 2018


Extraordinarily Robust Polyproline Type I Peptoid Helices Generated via the Incorporation of α-Chiral Aromatic N -1-Naphthylethyl Side Chains
journal, October 2011


Peptoid Polymers: A Highly Designable Bioinspired Material
journal, May 2013


Structure–Conductivity Relationship for Peptoid-Based PEO–Mimetic Polymer Electrolytes
journal, June 2012


Self-assembly of crystalline nanotubes from monodisperse amphiphilic diblock copolypeptoid tiles
journal, March 2016


Morphology and Proton Transport in Humidified Phosphonated Peptoid Block Copolymers
journal, April 2016


High-Throughput Sequencing of Peptoids and Peptide−Peptoid Hybrids by Partial Edman Degradation and Mass Spectrometry
journal, March 2009


New submonomers for poly N-substituted glycines (peptoids)
journal, February 1999


DNA origami protection and molecular interfacing through engineered sequence-defined peptoids
journal, March 2020


The design, synthesis, and evaluation of molecules that enable or enhance cellular uptake: Peptoid molecular transporters
journal, November 2000


Cooperative Intramolecular Hydrogen Bonding Strongly Enforces cis -Peptoid Folding
journal, November 2019


Peptoid Oligomers with α-Chiral, Aromatic Side Chains:  Effects of Chain Length on Secondary Structure
journal, April 2001


Diblock copolypeptoids: a review of phase separation, crystallization, self-assembly and biological applications
journal, January 2020


Synthesis and Characterization of Well-Defined PEGylated Polypeptoids as Protein-Resistant Polymers
journal, February 2017


Atomic-level engineering and imaging of polypeptoid crystal lattices
journal, October 2019


A Universal Method for Detection of Amyloidogenic Misfolded Proteins
journal, May 2011


Efficient method for the preparation of peptoids [oligo(N-substituted glycines)] by submonomer solid-phase synthesis
journal, December 1992


Discovery of Nanomolar Ligands for 7-Transmembrane G-Protein-Coupled Receptors from a Diverse N-(Substituted)glycine Peptoid Library
journal, August 1994