Solid‐phase synthesis of three‐armed star‐shaped peptoids and their hierarchical self‐assembly
Abstract
Due to the branched structure feature and unique properties, a variety of star‐shaped polymers have been designed and synthesized. Despite those advances, solid‐phase synthesis of star‐shaped sequence‐defined synthetic polymers that exhibit hierarchical self‐assembly remains a significant challenge. Hence, we present an effective strategy for the solid‐phase synthesis of three‐armed star‐shaped peptoids, in which ethylenediamine was used as the centric star pivot. Based on the sequence of monomer addition, a series of AA′A′′‐type and ABB′‐type peptoids were synthesized and characterized by UPLC‐MS (ultrahigh performance liquid chromatography‐mass spectrometry). By taking advantage of the easy‐synthesis and large side‐chain diversity, we synthesized star‐shaped peptoids with tunable functions. We further demonstrated the aqueous self‐assembly of some representative peptoids into biomimetic nanomaterials with well‐defined hierarchical structures, such as nanofibers and nanotubes. These results indicate that star‐shaped peptoids offer the potential in self‐assembly of biomimetic nanomaterials with tunable chemistries and functions.
- Authors:
-
- Physical Sciences Division Pacific Northwest National Laboratory Richland Western Australia
- Physical Sciences Division Pacific Northwest National Laboratory Richland Western Australia, Institute of Rheological Mechanics Xiangtan University Xiangtan Hunan China
- Physical Sciences Division Pacific Northwest National Laboratory Richland Western Australia, Department of Mechanical Engineering and Materials Science and Engineering Program State University of New York Binghamton New York
- Physical Sciences Division Pacific Northwest National Laboratory Richland Western Australia, College of Chemistry and Chemical Engineering Jiangxi Normal University Nanchang Jiangxi China
- Publication Date:
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1491957
- Resource Type:
- Publisher's Accepted Manuscript
- Journal Name:
- Biopolymers
- Additional Journal Information:
- Journal Name: Biopolymers Journal Volume: 110 Journal Issue: 4; Journal ID: ISSN 0006-3525
- Publisher:
- Wiley Blackwell (John Wiley & Sons)
- Country of Publication:
- United States
- Language:
- English
Citation Formats
Jin, Haibao, Jian, Tengyue, Ding, Yan‐Huai, Chen, Yulin, Mu, Peng, Wang, Lei, and Chen, Chun‐Long. Solid‐phase synthesis of three‐armed star‐shaped peptoids and their hierarchical self‐assembly. United States: N. p., 2019.
Web. doi:10.1002/bip.23258.
Jin, Haibao, Jian, Tengyue, Ding, Yan‐Huai, Chen, Yulin, Mu, Peng, Wang, Lei, & Chen, Chun‐Long. Solid‐phase synthesis of three‐armed star‐shaped peptoids and their hierarchical self‐assembly. United States. https://doi.org/10.1002/bip.23258
Jin, Haibao, Jian, Tengyue, Ding, Yan‐Huai, Chen, Yulin, Mu, Peng, Wang, Lei, and Chen, Chun‐Long. Thu .
"Solid‐phase synthesis of three‐armed star‐shaped peptoids and their hierarchical self‐assembly". United States. https://doi.org/10.1002/bip.23258.
@article{osti_1491957,
title = {Solid‐phase synthesis of three‐armed star‐shaped peptoids and their hierarchical self‐assembly},
author = {Jin, Haibao and Jian, Tengyue and Ding, Yan‐Huai and Chen, Yulin and Mu, Peng and Wang, Lei and Chen, Chun‐Long},
abstractNote = {Due to the branched structure feature and unique properties, a variety of star‐shaped polymers have been designed and synthesized. Despite those advances, solid‐phase synthesis of star‐shaped sequence‐defined synthetic polymers that exhibit hierarchical self‐assembly remains a significant challenge. Hence, we present an effective strategy for the solid‐phase synthesis of three‐armed star‐shaped peptoids, in which ethylenediamine was used as the centric star pivot. Based on the sequence of monomer addition, a series of AA′A′′‐type and ABB′‐type peptoids were synthesized and characterized by UPLC‐MS (ultrahigh performance liquid chromatography‐mass spectrometry). By taking advantage of the easy‐synthesis and large side‐chain diversity, we synthesized star‐shaped peptoids with tunable functions. We further demonstrated the aqueous self‐assembly of some representative peptoids into biomimetic nanomaterials with well‐defined hierarchical structures, such as nanofibers and nanotubes. These results indicate that star‐shaped peptoids offer the potential in self‐assembly of biomimetic nanomaterials with tunable chemistries and functions.},
doi = {10.1002/bip.23258},
journal = {Biopolymers},
number = 4,
volume = 110,
place = {United States},
year = {Thu Jan 24 00:00:00 EST 2019},
month = {Thu Jan 24 00:00:00 EST 2019}
}
https://doi.org/10.1002/bip.23258
Web of Science
Works referenced in this record:
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
Artificial Peptide-Nanospheres Self-Assembled from Three-Way Junctions of β-Sheet-Forming Peptides
journal, July 2005
- Matsuura, Kazunori; Murasato, Kazuya; Kimizuka, Nobuo
- Journal of the American Chemical Society, Vol. 127, Issue 29
Combating multidrug-resistant Gram-negative bacteria with structurally nanoengineered antimicrobial peptide polymers
journal, September 2016
- Lam, Shu J.; O'Brien-Simpson, Neil M.; Pantarat, Namfon
- Nature Microbiology, Vol. 1, Issue 11
Star-shaped π-conjugated oligomers and their applications in organic electronics and photonics
journal, January 2010
- Kanibolotsky, Alexander L.; Perepichka, Igor F.; Skabara, Peter J.
- Chemical Society Reviews, Vol. 39, Issue 7, p. 2695-2728
Structure-Based Design of Inhibitors of Protein-Protein Interactions: Mimicking Peptide Binding Epitopes
journal, June 2015
- Pelay-Gimeno, Marta; Glas, Adrian; Koch, Oliver
- Angewandte Chemie International Edition, Vol. 54, Issue 31
Sequence-Controlled Polymers
journal, August 2013
- Lutz, J. -F.; Ouchi, M.; Liu, D. R.
- Science, Vol. 341, Issue 6146
Peptoid Polymers: A Highly Designable Bioinspired Material
journal, May 2013
- Sun, Jing; Zuckermann, Ronald N.
- ACS Nano, Vol. 7, Issue 6
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
Highly stable and self-repairing membrane-mimetic 2D nanomaterials assembled from lipid-like peptoids
journal, July 2016
- Jin, Haibao; Jiao, Fang; Daily, Michael D.
- Nature Communications, Vol. 7, Issue 1
Biocompatible or biodegradable hyperbranched polymers: from self-assembly to cytomimetic applications
journal, January 2012
- Jin, Haibao; Huang, Wei; Zhu, Xinyuan
- Chemical Society Reviews, Vol. 41, Issue 18
Reversible and Large-Scale Cytomimetic Vesicle Aggregation: Light-Responsive Host-Guest Interactions
journal, September 2011
- Jin, Haibao; Zheng, Yongli; Liu, Yong
- Angewandte Chemie International Edition, Vol. 50, Issue 44
Synthesis of functional polymers with controlled architecture by CRP of monomers in the presence of cross-linkers: From stars to gels
journal, April 2009
- Gao, Haifeng; Matyjaszewski, Krzysztof
- Progress in Polymer Science, Vol. 34, Issue 4
Designable and dynamic single-walled stiff nanotubes assembled from sequence-defined peptoids
journal, January 2018
- Jin, Haibao; Ding, Yan-Huai; Wang, Mingming
- Nature Communications, Vol. 9, Issue 1
Tunable assembly of biomimetic peptoids as templates to control nanostructure catalytic activity
journal, January 2018
- Merrill, Nicholas A.; Yan, Feng; Jin, Haibao
- Nanoscale, Vol. 10, Issue 26
Protected thiol strategies in macromolecular design
journal, January 2017
- Goethals, Fabienne; Frank, Daniel; Du Prez, Filip
- Progress in Polymer Science, Vol. 64
Leucine-Based Polymer Architecture-Induced Antimicrobial Properties and Bacterial Cell Morphology Switching
journal, January 2018
- Mukherjee, Ishita; Ghosh, Anwesha; Bhadury, Punyasloke
- ACS Omega, Vol. 3, Issue 1
Functional Supramolecular Polymers
journal, February 2012
- Aida, T.; Meijer, E. W.; Stupp, S. I.
- Science, Vol. 335, Issue 6070
Star polymers: Advances in biomedical applications
journal, July 2015
- Wu, Wei; Wang, Weigang; Li, Jianshu
- Progress in Polymer Science, Vol. 46
Stimuli-responsive star polymers
journal, April 2013
- Kuckling, Dirk; Wycisk, Agnes
- Journal of Polymer Science Part A: Polymer Chemistry, Vol. 51, Issue 14
Tuning crystallization pathways through sequence engineering of biomimetic polymers
journal, April 2017
- Ma, Xiang; Zhang, Shuai; Jiao, Fang
- Nature Materials, Vol. 16, Issue 7
A Dynamic Duo: Pairing Click Chemistry and Postpolymerization Modification To Design Complex Surfaces
journal, August 2014
- Arnold, Rachelle M.; Patton, Derek L.; Popik, Vladimir V.
- Accounts of Chemical Research, Vol. 47, Issue 10
Hierarchical Self-Assembly of a Biomimetic Diblock Copolypeptoid into Homochiral Superhelices
journal, November 2010
- Murnen, Hannah K.; Rosales, Adrianne M.; Jaworski, Jonathan N.
- Journal of the American Chemical Society, Vol. 132, Issue 45
Sequence-Specific Peptide Synthesis by an Artificial Small-Molecule Machine
journal, January 2013
- Lewandowski, B.; De Bo, G.; Ward, J. W.
- Science, Vol. 339, Issue 6116
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
Targeting ETS1 with RNAi-based supramolecular nanoassemblies for multidrug-resistant breast cancer therapy
journal, May 2017
- Wu, Min; Liu, Xingang; Jin, Weihong
- Journal of Controlled Release, Vol. 253
Dendrimer-Type Peptoid-Decorated Hexaphenylxylenes and Tetraphenylmethanes: Synthesis and Structure in Solution and in the Gas Phase
journal, October 2014
- Peschko, Katharina; Schade, Alexandra; Vollrath, Sidonie B. L.
- Chemistry - A European Journal, Vol. 20, Issue 49
Design, Synthesis, Assembly, and Engineering of Peptoid Nanosheets
journal, January 2016
- Robertson, Ellen J.; Battigelli, Alessia; Proulx, Caroline
- Accounts of Chemical Research, Vol. 49, Issue 3
Development of Star Polymers as Unimolecular Containers for Nanomaterials
journal, March 2012
- Gao, Haifeng
- Macromolecular Rapid Communications, Vol. 33, Issue 9
Star Polymers
journal, June 2016
- Ren, Jing M.; McKenzie, Thomas G.; Fu, Qiang
- Chemical Reviews, Vol. 116, Issue 12
Star-Shaped Polypeptides: Synthesis and Opportunities for Delivery of Therapeutics
journal, September 2015
- Byrne, Mark; Murphy, Robert; Kapetanakis, Antonios
- Macromolecular Rapid Communications, Vol. 36, Issue 21
Emerging applications of stimuli-responsive polymer materials
journal, January 2010
- Stuart, Martien A. Cohen; Huck, Wilhelm T. S.; Genzer, Jan
- Nature Materials, Vol. 9, Issue 2, p. 101-113
Sequence Programmable Peptoid Polymers for Diverse Materials Applications
journal, April 2015
- Knight, Abigail S.; Zhou, Effie Y.; Francis, Matthew B.
- Advanced Materials, Vol. 27, Issue 38
Structural basis of human PCNA sliding on DNA
journal, January 2017
- De March, Matteo; Merino, Nekane; Barrera-Vilarmau, Susana
- Nature Communications, Vol. 8, Issue 1
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
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
Miktoarm star polymers: advances in synthesis, self-assembly, and applications
journal, January 2010
- Khanna, Kunal; Varshney, Sunil; Kakkar, Ashok
- Polymer Chemistry, Vol. 1, Issue 8
Supramolecular shape memory hydrogels: a new bridge between stimuli-responsive polymers and supramolecular chemistry
journal, January 2017
- Lu, Wei; Le, Xiaoxia; Zhang, Jiawei
- Chemical Society Reviews, Vol. 46, Issue 5
Guest Inclusion and Structural Dynamics in 2-D Hydrogen-Bonded Metal−Organic Frameworks
journal, December 2008
- Chen, Chun-Long; Beatty, Alicia M.
- Journal of the American Chemical Society, Vol. 130, Issue 51
Self-Assembling Cages from Coiled-Coil Peptide Modules
journal, April 2013
- Fletcher, J. M.; Harniman, R. L.; Barnes, F. R. H.
- Science, Vol. 340, Issue 6132
Positional Scanning for Peptide Secondary Structure by Systematic Solid-Phase Synthesis of Amino Lactam Peptides
journal, June 2009
- Jamieson, Andrew G.; Boutard, Nicolas; Beauregard, Kim
- Journal of the American Chemical Society, Vol. 131, Issue 22
Peptoids and Polypeptoids at the Frontier of Supra- and Macromolecular Engineering
journal, December 2015
- Gangloff, Niklas; Ulbricht, Juliane; Lorson, Thomas
- Chemical Reviews, Vol. 116, Issue 4