Hierarchical assemblies of polypeptoids for rational design of advanced functional nanomaterials
Abstract
Abstract Polypeptoids (poly‐N‐substituent glycines) are a class of highly tailorable peptidomimetic polymers. Polypeptoids have identical backbones as polypeptides (poly‐C‐substituent glycines), but sidechains of polypeptoids are appended to backbone nitrogen rather than α‐carbon of polypeptides. As a result, peptoid backbone lacks of chirality and hydrogen bond donors. This unique structure gives polypeptoids a combined merit of both high stability as synthetic polymers and biocompatibility as biopolymers. In addition, peptoid sequences can be engineered precisely to assemble specific crystalline patterns such as spheres, fibers, ribbons, tubes, and sheets, which shows promising potentials of polypeptoids for different applications such as antimicrobials, catalysts, drug delivery, and templating inorganic materials. In this review, we summarize recent investigations into hierarchical self‐assembly pathways and molecular structures of peptoid crystals that are of interest as templates for fabricating functional materials for potential biomedical, biochemical, and bioengineering applications. This review provides a summary of recent experimental and computational studies of polypeptoid assembly in solution and solid‐liquid interfaces, current achievements in the field, and discusses future challenges and opportunities for the rational design of self‐assembled polypeptoid nanomaterials.
- Authors:
-
- Univ. of Chicago, IL (United States)
- Publication Date:
- Research Org.:
- Univ. of Washington, Seattle, WA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1823072
- Alternate Identifier(s):
- OSTI ID: 1814039
- Grant/Contract Number:
- SC0019288; DE‐SC0019288
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Biopolymers
- Additional Journal Information:
- Journal Volume: 112; Journal Issue: 9; Journal ID: ISSN 0006-3525
- Publisher:
- Wiley
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 36 MATERIALS SCIENCE
Citation Formats
Zhao, Mingfei. Hierarchical assemblies of polypeptoids for rational design of advanced functional nanomaterials. United States: N. p., 2021.
Web. doi:10.1002/bip.23469.
Zhao, Mingfei. Hierarchical assemblies of polypeptoids for rational design of advanced functional nanomaterials. United States. https://doi.org/10.1002/bip.23469
Zhao, Mingfei. Wed .
"Hierarchical assemblies of polypeptoids for rational design of advanced functional nanomaterials". United States. https://doi.org/10.1002/bip.23469. https://www.osti.gov/servlets/purl/1823072.
@article{osti_1823072,
title = {Hierarchical assemblies of polypeptoids for rational design of advanced functional nanomaterials},
author = {Zhao, Mingfei},
abstractNote = {Abstract Polypeptoids (poly‐N‐substituent glycines) are a class of highly tailorable peptidomimetic polymers. Polypeptoids have identical backbones as polypeptides (poly‐C‐substituent glycines), but sidechains of polypeptoids are appended to backbone nitrogen rather than α‐carbon of polypeptides. As a result, peptoid backbone lacks of chirality and hydrogen bond donors. This unique structure gives polypeptoids a combined merit of both high stability as synthetic polymers and biocompatibility as biopolymers. In addition, peptoid sequences can be engineered precisely to assemble specific crystalline patterns such as spheres, fibers, ribbons, tubes, and sheets, which shows promising potentials of polypeptoids for different applications such as antimicrobials, catalysts, drug delivery, and templating inorganic materials. In this review, we summarize recent investigations into hierarchical self‐assembly pathways and molecular structures of peptoid crystals that are of interest as templates for fabricating functional materials for potential biomedical, biochemical, and bioengineering applications. This review provides a summary of recent experimental and computational studies of polypeptoid assembly in solution and solid‐liquid interfaces, current achievements in the field, and discusses future challenges and opportunities for the rational design of self‐assembled polypeptoid nanomaterials.},
doi = {10.1002/bip.23469},
journal = {Biopolymers},
number = 9,
volume = 112,
place = {United States},
year = {Wed Aug 18 00:00:00 EDT 2021},
month = {Wed Aug 18 00:00:00 EDT 2021}
}
Works referenced in this record:
Peptoids that mimic the structure, function, and mechanism of helical antimicrobial peptides
journal, February 2008
- Chongsiriwatana, N. P.; Patch, J. A.; Czyzewski, A. M.
- Proceedings of the National Academy of Sciences, Vol. 105, Issue 8
Casting Metal Nanowires Within Discrete Self-Assembled Peptide Nanotubes
journal, April 2003
- Reches, M.
- Science, Vol. 300, Issue 5619
Molecular modeling studies of peptoid polymers
journal, January 2017
- J. Weiser, Laura; E. Santiso, Erik
- AIMS Materials Science, Vol. 4, Issue 5
Development and use of an atomistic CHARMM-based forcefield for peptoid simulation
journal, November 2013
- Mirijanian, Dina T.; Mannige, Ranjan V.; Zuckermann, Ronald N.
- Journal of Computational Chemistry, Vol. 35, Issue 5
Self-assembly of crystalline nanotubes from monodisperse amphiphilic diblock copolypeptoid tiles
journal, March 2016
- Sun, Jing; Jiang, Xi; Lund, Reidar
- Proceedings of the National Academy of Sciences, Vol. 113, Issue 15
Proteolytic studies of homologous peptide and N-substituted glycine peptoid oligomers
journal, November 1994
- Miller, Susan M.; Simon, Reyna J.; Ng, Simon
- Bioorganic & Medicinal Chemistry Letters, Vol. 4, Issue 22
A CGenFF‐based force field for simulations of peptoids with both cis and trans peptide bonds
journal, May 2019
- Weiser, Laura J.; Santiso, Erik E.
- Journal of Computational Chemistry, Vol. 40, Issue 22
Kinetics and Equilibria of Cis/Trans Isomerization of Backbone Amide Bonds in Peptoids
journal, October 2007
- Sui, Qiang; Borchardt, Dan; Rabenstein, Dallas L.
- Journal of the American Chemical Society, Vol. 129, Issue 39
Synthesis and Characterization of Cleavable Core-Cross-Linked Micelles Based on Amphiphilic Block Copolypeptoids as Smart Drug Carriers
journal, February 2016
- Li, Ang; Zhang, Donghui
- Biomacromolecules, Vol. 17, Issue 3
Universal Relationship between Molecular Structure and Crystal Structure in Peptoid Polymers and Prevalence of the cis Backbone Conformation
journal, January 2018
- Greer, Douglas R.; Stolberg, Michael A.; Kundu, Joyjit
- Journal of the American Chemical Society, Vol. 140, Issue 2
Designed Peptoids as Tunable Modifiers of Zeolite Crystallization
journal, October 2017
- Li, Rui; Smolyakova, Alisa; Maayan, Galia
- Chemistry of Materials, Vol. 29, Issue 21
Supramolecular Nanosheets Assembled from Poly(ethylene glycol)- b -poly( N -(2-phenylethyl)glycine) Diblock Copolymer Containing Crystallizable Hydrophobic Polypeptoid: Crystallization Driven Assembly Transition from Filaments to Nanosheets
journal, February 2019
- Wei, Yuhan; Tian, Jiliang; Zhang, Zekun
- Macromolecules, Vol. 52, Issue 4
Polypeptoid polymers: Synthesis, characterization, and properties
journal, October 2017
- Chan, Brandon A.; Xuan, Sunting; Li, Ang
- Biopolymers, Vol. 109, Issue 1
Implicit-Solvent Coarse-Grained Simulation with a Fluctuating Interface Reveals a Molecular Mechanism for Peptoid Monolayer Buckling
journal, December 2015
- Haxton, Thomas K.; Zuckermann, Ronald N.; Whitelam, Stephen
- Journal of Chemical Theory and Computation, Vol. 12, Issue 1
Supramolecular biomaterials
journal, December 2015
- Webber, Matthew J.; Appel, Eric A.; Meijer, E. W.
- Nature Materials, Vol. 15, Issue 1
Peptoid-Based Programmable 2D Nanomaterial Sensor for Selective and Sensitive Detection of H 2 S in Live Cells
journal, August 2020
- Wang, Mingming; Song, Yang; Mu, Peng
- ACS Applied Bio Materials, Vol. 3, Issue 9
Crystallization-Driven Two-Dimensional Nanosheet from Hierarchical Self-Assembly of Polypeptoid-Based Diblock Copolymers
journal, August 2018
- Shi, Zhekun; Wei, Yuhan; Zhu, Chenhui
- Macromolecules, Vol. 51, Issue 16
Control of Crystallization and Melting Behavior in Sequence Specific Polypeptoids
journal, July 2010
- Rosales, Adrianne M.; Murnen, Hannah K.; Zuckermann, Ronald N.
- Macromolecules, Vol. 43, Issue 13
Structural absorption by barbule microstructures of super black bird of paradise feathers
journal, January 2018
- McCoy, Dakota E.; Feo, Teresa; Harvey, Todd Alan
- Nature Communications, Vol. 9, Issue 1
Conformations of peptoids in nanosheets result from the interplay of backbone energetics and intermolecular interactions
journal, May 2018
- Edison, John R.; Spencer, Ryan K.; Butterfoss, Glenn L.
- Proceedings of the National Academy of Sciences, Vol. 115, Issue 22
Discovery of Stable and Selective Antibody Mimetics from Combinatorial Libraries of Polyvalent, Loop-Functionalized Peptoid Nanosheets
journal, December 2019
- Kim, Jae Hong; Kim, Samuel C.; Kline, Mark A.
- ACS Nano
Bioinspired Peptoid Nanotubes for Targeted Tumor Cell Imaging and Chemo‐Photodynamic Therapy
journal, August 2019
- Luo, Yanan; Song, Yang; Wang, Mingming
- Small, Vol. 15, Issue 43
Crystallization and lamellar nanosheet formation of an aromatic dipeptoid
journal, January 2019
- Castelletto, Valeria; Chippindale, Ann M.; Hamley, Ian W.
- Chemical Communications, Vol. 55, Issue 42
Self-Assembly of Minimal Peptoid Sequences
journal, March 2020
- Castelletto, Valeria; Seitsonen, Jani; Tewari, Kunal M.
- ACS Macro Letters, Vol. 9, Issue 4
Peptoid nanosheets exhibit a new secondary-structure motif
journal, October 2015
- Mannige, Ranjan V.; Haxton, Thomas K.; Proulx, Caroline
- Nature, Vol. 526, Issue 7573
Hierarchical supramolecular assembly of a single peptoid polymer into a planar nanobrush with two distinct molecular packing motifs
journal, December 2020
- Sun, Jing; Wang, Zhiwei; Zhu, Chenhui
- Proceedings of the National Academy of Sciences, Vol. 117, Issue 50
Towards a coarse-grained model of the peptoid backbone: the case of N , N -dimethylacetamide
journal, January 2018
- Du, Pu; Rick, Steven W.; Kumar, Revati
- Physical Chemistry Chemical Physics, Vol. 20, Issue 36
MARTINI-Compatible Coarse-Grained Model for the Mesoscale Simulation of Peptoids
journal, August 2020
- Zhao, Mingfei; Sampath, Janani; Alamdari, Sarah
- The Journal of Physical Chemistry B, Vol. 124, Issue 36
Crystallization-Driven Self-Assembly of Coil–Comb-Shaped Polypeptoid Block Copolymers: Solution Morphology and Self-Assembly Pathways
journal, November 2019
- Jiang, Naisheng; Yu, Tianyi; Darvish, Omead A.
- Macromolecules, Vol. 52, Issue 22
A moisture function of soil heterotrophic respiration that incorporates microscale processes
journal, July 2018
- Yan, Zhifeng; Bond-Lamberty, Ben; Todd-Brown, Katherine E.
- Nature Communications, Vol. 9, Issue 1
Free-floating ultrathin two-dimensional crystals from sequence-specific peptoid polymers
journal, April 2010
- Nam, Ki Tae; Shelby, Sarah A.; Choi, Philip H.
- Nature Materials, Vol. 9, Issue 5
Atomic-level engineering and imaging of polypeptoid crystal lattices
journal, October 2019
- Xuan, Sunting; Jiang, Xi; Spencer, Ryan K.
- Proceedings of the National Academy of Sciences, Vol. 116, Issue 45
Peptoid Polymers: A Highly Designable Bioinspired Material
journal, May 2013
- Sun, Jing; Zuckermann, Ronald N.
- ACS Nano, Vol. 7, Issue 6
Self-assembly of ultra-small micelles from amphiphilic lipopeptoids
journal, January 2017
- Lau, King Hang Aaron; Castelletto, Valeria; Kendall, Thomas
- Chemical Communications, Vol. 53, Issue 13
Modulating the Molecular Geometry and Solution Self-Assembly of Amphiphilic Polypeptoid Block Copolymers by Side Chain Branching Pattern
journal, April 2021
- Kang, Liying; Chao, Albert; Zhang, Meng
- Journal of the American Chemical Society, Vol. 143, Issue 15
Solution Self-Assemblies of Sequence-Defined Ionic Peptoid Block Copolymers
journal, February 2018
- Sternhagen, Garrett L.; Gupta, Sudipta; Zhang, Yueheng
- Journal of the American Chemical Society, Vol. 140, Issue 11
Glycosylated Peptoid Nanosheets as a Multivalent Scaffold for Protein Recognition
journal, February 2018
- Battigelli, Alessia; Kim, Jae Hong; Dehigaspitiya, Dilani C.
- ACS Nano, Vol. 12, Issue 3
Nanoparticle-Mediated Assembly of Peptoid Nanosheets Functionalized with Solid-Binding Proteins: Designing Heterostructures for Hierarchy
journal, February 2021
- Ma, Jinrong; Cai, Bin; Zhang, Shuai
- Nano Letters, Vol. 21, Issue 4
Tuning crystallization pathways through sequence engineering of biomimetic polymers
journal, April 2017
- Ma, Xiang; Zhang, Shuai; Jiao, Fang
- Nature Materials, Vol. 16, Issue 7
Efficient method for the preparation of peptoids [oligo(N-substituted glycines)] by submonomer solid-phase synthesis
journal, December 1992
- Zuckermann, Ronald N.; Kerr, Janice M.; Kent, Stephen B. H.
- Journal of the American Chemical Society, Vol. 114, Issue 26
Shaken, Not Stirred: Collapsing a Peptoid Monolayer To Produce Free-Floating, Stable Nanosheets
journal, December 2011
- Sanii, Babak; Kudirka, Romas; Cho, Andrew
- Journal of the American Chemical Society, Vol. 133, Issue 51
Folding of a single-chain, information-rich polypeptoid sequence into a highly ordered nanosheet
journal, January 2011
- Kudirka, Romas; Tran, Helen; Sanii, Babak
- Biopolymers, Vol. 96, Issue 5
Efficient Cytosolic Delivery Using Crystalline Nanoflowers Assembled from Fluorinated Peptoids
journal, November 2018
- Song, Yang; Wang, Mingming; Li, Suiqiong
- Small, Vol. 14, Issue 52
Synthesis and Characterization of Well-Defined PEGylated Polypeptoids as Protein-Resistant Polymers
journal, February 2017
- Xuan, Sunting; Gupta, Sudipta; Li, Xin
- Biomacromolecules, Vol. 18, Issue 3
Self-Repair and Patterning of 2D Membrane-Like Peptoid Materials
journal, August 2016
- Jiao, Fang; Chen, Yulin; Jin, Haibao
- Advanced Functional Materials, Vol. 26, Issue 48
Molecular Engineering of the Peptoid Nanosheet Hydrophobic Core
journal, October 2016
- Robertson, Ellen J.; Proulx, Caroline; Su, Jessica K.
- Langmuir, Vol. 32, Issue 45
Evidence for cis Amide Bonds in Peptoid Nanosheets
journal, April 2018
- Hudson, Benjamin C.; Battigelli, Alessia; Connolly, Michael D.
- The Journal of Physical Chemistry Letters, Vol. 9, Issue 10
A point-charge force field for molecular mechanics simulations of proteins based on condensed-phase quantum mechanical calculations
journal, October 2003
- Duan, Yong; Wu, Chun; Chowdhury, Shibasish
- Journal of Computational Chemistry, Vol. 24, Issue 16
Structure-Determining Step in the Hierarchical Assembly of Peptoid Nanosheets
journal, October 2014
- Sanii, Babak; Haxton, Thomas K.; Olivier, Gloria K.
- ACS Nano, Vol. 8, Issue 11
Surface-Directed Assembly of Sequence-Defined Synthetic Polymers into Networks of Hexagonally Patterned Nanoribbons with Controlled Functionalities
journal, May 2016
- Chen, Chun-Long; Zuckermann, Ronald N.; DeYoreo, James J.
- ACS Nano, Vol. 10, Issue 5