Processable Cyclic Peptide Nanotubes with Tunable Interiors

Published on Sep 14, 2011in Journal of the American Chemical Society14.612
· DOI :10.1021/JA2063082
Rami Hourani10
Estimated H-index: 10
(University of California, Berkeley),
Chen Zhang2
Estimated H-index: 2
(University of California, Berkeley)
+ 5 AuthorsTing Xu39
Estimated H-index: 39
(University of California, Berkeley)
Sources
Abstract
A facile route to generate cyclic peptide nanotubes with tunable interiors is presented. By incorporating 3-amino-2-methylbenzoic acid in the d,l-alternating primary sequence of a cyclic peptide, a functional group can be presented in the interior of the nanotubes without compromising the formation of high aspect ratio nanotubes. The new design of such a cyclic peptide also enables one to modulate the nanotube growth process to be compatible with the polymer processing window without compromising the formation of high aspect ratio nanotubes, thus opening a viable approach toward molecularly defined porous membranes.
📖 Papers frequently viewed together
199342.78Nature
1,398 Citations
199442.78Nature
3 Authors (M. R. Ghadiri, ..., L. K. Buehler)
789 Citations
201114.59ACS Nano
8 Authors (Ting Xu, ..., Brett A. Helms)
88 Citations
References39
Newest
#1Douglas L. Gin (CU: University of Colorado Boulder)H-Index: 60
#2Richard D. Noble (CU: University of Colorado Boulder)H-Index: 95
Synthetic membranes are used in many separation processes, from industrial-scale ones—such as separating atmospheric gases for medical and industrial use, and removing salt from seawater—to smaller-scale processes in chemical synthesis and purification. Membranes are commonly solid materials, such as polymers, that have good mechanical stability and can be readily processed into high–surface area, defect-free, thin films. These features are critical for obtaining not only good chemical separatio...
490 CitationsSource
#1Ting Xu (University of California, Berkeley)H-Index: 39
#2Nana ZhaoH-Index: 1
Last. Brett A. HelmsH-Index: 38
view all 8 authors...
Porous thin films containing subnanometer channels oriented normal to the surface exhibit unique transport and separation properties and can serve as selective membranes for separation and protective coatings. While molecularly defined nanoporous inorganic and organic materials abound, generating flexible nanoporous thin films with highly aligned channels over large areas has been elusive. Here, we developed a new approach where the growth of cyclic peptide nanotubes can be directed in a structu...
88 CitationsSource
#1Roberto J. Brea (University of Santiago de Compostela)H-Index: 17
#2César Reiriz (University of Santiago de Compostela)H-Index: 3
Last. Juan R. Granja (University of Santiago de Compostela)H-Index: 35
view all 3 authors...
In recent years, considerable effort has been devoted to the preparation of artificial nanotubular materials. One of the most successful approaches for the construction of noncovalently bonded nanotube entities is the self-assembly of cyclic polypeptides in stacks that are stabilized by hydrogen bonds. This tutorial review covers the history and current situation for synthetic organic nanostructures obtained from self-assembling cyclic peptides. In particular, we describe the evolution to cyclic...
207 CitationsSource
#1Andrei L. Kholkin (University of Aveiro)H-Index: 64
#2Nadav AmdurskyH-Index: 25
Last. Gil RosenmanH-Index: 50
view all 5 authors...
We show anomalously strong shear piezoelectric activity in self-assembled diphenylalanine peptide nanotubes (PNTs), indicating electric polarization directed along the tube axis. Comparison with well-known piezoelectric LiNbO3 and lateral signal calibration yields sufficiently high effective piezoelectric coefficient values of at least 60 pm/V (shear response for tubes of ≈200 nm in diameter). PNTs demonstrate linear deformation without irreversible degradation in a broad range of driving voltag...
271 CitationsSource
#1César Reiriz (CSIC: Spanish National Research Council)H-Index: 1
#2Manuel Amorín (CSIC: Spanish National Research Council)H-Index: 4
Last. Juan R. Granja (CSIC: Spanish National Research Council)H-Index: 35
view all 5 authors...
Here we describe a self-assembling α,γ-cyclic tetrapeptide that contains the 4-amino-3-hydroxytetrahydrofuran-2-carboxylic acid, in which the hydroxy group is pointing towards the inner cavity of the resulting dimers.
41 CitationsSource
#1César Reiriz (University of Santiago de Compostela)H-Index: 3
#2Roberto J. BreaH-Index: 17
Last. Juan R. GranjaH-Index: 35
view all 10 authors...
The formation and full characterization of single self-assembling α,γ-peptide nanotubes (α,γ-SPNs) is described. The introduction of C60 into cyclic peptides allows the preparation of supramolecular 1D fullerene arrangements induced by peptide nanotube formation under appropriate conditions.
76 CitationsSource
#1Stefan Kubik (TUK: Kaiserslautern University of Technology)H-Index: 30
Nature has devised highly efficient and selective ways of recognizing anionic substrates by using surprisingly few building blocks the most important of which are the amino acids serine, tryptophane, and arginine in addition to NH groups along the protein backbone. Deliberate use of amino acids for the construction of abiotic anion receptors could lead to systems that mimic the anion coordinating properties of anion binding proteins. With this aim in mind several groups have focused their attent...
222 CitationsSource
#1Ling Zang (SIU: Southern Illinois University Carbondale)H-Index: 55
#2Yanke Che (SIU: Southern Illinois University Carbondale)H-Index: 32
Last. Jeffrey S. MooreH-Index: 121
view all 3 authors...
In general, fabrication of well-defined organic nanowires or nanobelts with controllable size and morphology is not as advanced as for their inorganic counterparts. Whereas inorganic nanowires are widely exploited in optoelectronic nanodevices, there remains considerable untapped potential in the one-dimensional (1D) organic materials. This Account describes our recent progress and discoveries in the field of 1D self-assembly of planar π-conjugated molecules and their application in various nano...
1,009 CitationsSource
#1Julien Couet (University of Freiburg)H-Index: 7
#2Markus Biesalski (University of Freiburg)H-Index: 29
: The external structure of polymer-wrapped nanotubes resembles that of small nanorods with a core/shell morphology, where the core consists of a self-assembled peptide nanotube surrounded by a soft polymeric coat. The length and the diameter of the nanorods are investigated as a function of the molar mass of the peptide-grafted macromolecules by statistical atomic force microscopy cross-section analysis of dry nanorods adsorbed to a solid substrate. With increasing molar mass of the grafted pol...
56 CitationsSource
#1Mark A. Shannon (UIUC: University of Illinois at Urbana–Champaign)H-Index: 42
#2Paul W. Bohn (ND: University of Notre Dame)H-Index: 1
Last. Anne M. Mayes (MIT: Massachusetts Institute of Technology)H-Index: 66
view all 6 authors...
This article highlights some of the science and technology being developed to improve the disinfection and decontamination of water, as well as efforts to increase water supplies through the safe reuse of wastewater and efficient desalination of sea and brackish water.
5,462 CitationsSource
Cited By110
Newest
#1Mitchell R. Silk (Monash University)H-Index: 2
#2Jason R. Price (ANSTO: Australian Nuclear Science and Technology Organisation)H-Index: 1
Last. David K. Chalmers (Monash University)H-Index: 23
view all 7 authors...
This is the peer reviewed version of the following article: Silk, Price, Mohanty, Leiros, Lund, Thompson, Chalmers. Side-Chain Interactions in d/l Peptide Nanotubes: Studies by Crystallography, NMR Spectroscopy and Molecular Dynamics. Chemistry - A European Journal. 2021, which has been published in final form at null https://doi.org/10.1002/chem.202102106 . This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This ...
Source
#1Hanne Mariën (Katholieke Universiteit Leuven)H-Index: 7
#2Rhea Verbeke (Katholieke Universiteit Leuven)H-Index: 9
Last. Pierre JacobsH-Index: 109
view all 3 authors...
23 CitationsSource
#1Qiao Song (Southern University of Science and Technology)H-Index: 13
#2Andrew Kerr (Warw.: University of Warwick)H-Index: 5
Last. Sébastien Perrier (Warw.: University of Warwick)H-Index: 69
view all 5 authors...
Supramolecular copolymers are an emerging class of materials, which bring together different properties and functionalities of multiple components via noncovalent interactions. While it is widely acknowledged that the repeating unit sequence plays an essential role on the performance of these materials, mastering and tuning the supramolecular copolymer sequence is still an open challenge. To date, only statistical supramolecular copolymers have been reported using cyclic peptide–polymer conjugat...
1 CitationsSource
#1Federica Novelli (University of Santiago de Compostela)H-Index: 1
#2Marcos Vilela (University of Santiago de Compostela)
Last. Juan R. Granja (University of Santiago de Compostela)H-Index: 35
view all 5 authors...
Light-induced molecular piping of cyclic peptide nanotubes to form bent tubular structures is described. The process is based on the [4+4] photocycloaddition of anthracene moieties, whose structural changes derived from the interdigitated flat disposition of precursors to the corresponding cycloadduct moieties, induced the geometrical modifications in nanotubes packing that provokes their curvature. For this purpose, we designed a new class of cyclic peptide nanotubes formed by β- and α-amino ac...
Source
#1Rajkumar Misra (TAU: Tel Aviv University)
#2Safra Rudnick-Glick (TAU: Tel Aviv University)H-Index: 4
Last. Lihi Adler-Abramovich (TAU: Tel Aviv University)H-Index: 34
view all 3 authors...
The engineering of biological molecules is the fundamental concept behind the design of complex materials with desirable functions. Over the last few decades, peptides and proteins have emerged as useful building blocks for well-defined nanostructures with controlled size and dimensions. Short peptides in particular have received much attention due to their inherent biocompatibility, lower synthetic cost, and ease of tunability. In addition to the diverse self-assembling properties of short pept...
Source
#1Zhenkai Cen (TJU: Tianjin University)
#2Lingyu Wang (TJU: Tianjin University)H-Index: 4
Last. Dandan Han (TJU: Tianjin University)H-Index: 11
view all 5 authors...
A gravimetric method is adopted to measure the solid–liquid equilibrium of 3-amino-2-methylbenzoic acid in different solvents, including methanol, ethanol, 1-propanol, isopropyl alcohol, 1-butanol,...
Source
#1HuaLong Chen (Capital Medical University)H-Index: 1
#2Yajing Liu (Capital Medical University)H-Index: 7
Last. Zehui Wu (Capital Medical University)H-Index: 5
view all 9 authors...
The m-pyridine urea (mPU) oligomer was constructed by using the intramolecular hydrogen bond formed by the pyridine nitrogen atom and the NH of urea and the intermolecular hydrogen bond of the terminal carbonyl group and the NH of urea. Due to the synergistic effect of hydrogen bonds, mPU oligomer folds and exhibits strong self-assembly behavior. Affected by folding, mPU oligomer generates a twisted plane, and one of its important features is that the carbonyl group of the urea group orientates ...
2 CitationsSource
#1Qiao Song (Warw.: University of Warwick)H-Index: 13
#2Zihe Cheng (Warw.: University of Warwick)H-Index: 1
Last. Sébastien Perrier (Warw.: University of Warwick)H-Index: 69
view all 7 authors...
This Review focuses on the establishment and development of self-assemblies governed by the supramolecular interactions between cyclic peptides. The Review first describes the type of cyclic peptides able to assemble into tubular structures to form supramolecular cyclic peptide nanotubes. A range of cyclic peptides have been identified to have such properties, including α-peptides, β-peptides, α,γ-peptides, and peptides based on δ- and e-amino acids. The Review covers the design and functionaliz...
4 CitationsSource
#1Martín Calvelo (University of Santiago de Compostela)H-Index: 4
#2Charlotte I. Lynch (University of Oxford)H-Index: 2
Last. Rebeca García-Fandiño (University of Santiago de Compostela)H-Index: 16
view all 5 authors...
Self-assembling cyclic peptide nanotubes can form nanopores when they are inserted in lipid bilayers, acting as ion and/or water permeable channels. In order to improve the versatility of these systems, it is possible to specifically design cyclic peptides with a combination of natural and non-natural amino acids, enabling the control of the nature of the inner cavity of the channels. Here, the behavior of two types of self-assembling peptide motifs, alternating α-amino acids with γ- or δ-aminoc...
3 CitationsSource
#1Julia Y. Rho (Warw.: University of Warwick)H-Index: 6
#2Sébastien Perrier (Warw.: University of Warwick)H-Index: 69
This Viewpoint highlights the design principles and development of peptide-based supramolecular polymers. Here we delve deep into the practicalities of synthesizing and characterizing these macromo...
3 CitationsSource