Self-assembling organic nanotubes based on a cyclic peptide architecture

Published on Nov 25, 1993in Nature49.962
· DOI :10.1038/366324A0
M. Reza Ghadiri74
Estimated H-index: 74
(Scripps Research Institute),
Juan R. Granja37
Estimated H-index: 37
(Scripps Research Institute)
+ 2 AuthorsNina Khazanovich3
Estimated H-index: 3
(Scripps Research Institute)
HOLLOW tubular structures of molecular dimensions may offer a variety of applications in chemistry, biochemistry and materials science. Concentric carbon nanotubes1,2 have attracted a great deal of attention, while the three-dimensional tubular pore structures of molecular sieves have long been exploited industrially3–8. Nanoscale tubes based on organic materials have also been reported previously9–13. Here we report the design, synthesis and characterization of a new class of organic nanotubes based on rationally designed cyclic polypeptides. When protonated, these compounds crystallize into tubular structures hundreds of nanometres long, with internal diameters of 7–8 A. Support for the proposed tubular structures is provided by electron microscopy, electron diffraction, Fourier-transform infrared spectroscopy and molecular modelling. These tubes are open-ended, with uniform shape and internal diameter. We anticipate that they may have possible applications in inclusion chemistry, catalysis, molecular electronics and molecular separation technology.
📖 Papers frequently viewed together
3 Authors (M. R. Ghadiri, ..., L. K. Buehler)
3 Authors (P. De Santis, ..., Roberto Rizzo)
#1Alain Monnier (UCSB: University of California, Santa Barbara)H-Index: 14
#2Ferdi Schüth (MPG: Max Planck Society)H-Index: 128
Last. Bradley F. Chmelka (UCSB: University of California, Santa Barbara)H-Index: 74
view all 12 authors...
A model is presented to explain the formation and morphologies of surfactant-silicate mesostructures. Three processes are identified: multidentate binding of silicate oligomers to the cationic surfactant, preferential silicate polymerization in the interface region, and charge density matching between the surfactant and the silicate. The model explains present experimental data, including the transformation between lamellar and hexagonal mesophases, and provides a guide for predicting conditions...
#1Akira Harada (Osaka University)H-Index: 84
#2Jun Li (Osaka University)H-Index: 106
Last. Mikiharu Kamachi (Osaka University)H-Index: 46
view all 3 authors...
MUCH attention has been focused recently on the design and fabrication of large-scale molecular structures1. Carbon nanotubes formed by an arc-discharge method2,3 have attracted particular attention. These tubes range from about 1 to 30 nanometres in diameter and a micrometre or so in length. To construct smaller tubes, direct chemical synthesis may be a more convenient approach. The cyclic oligomers of glucose known as cyclodextrins (CDs) would seem to be ideal candidates for the components of ...
#1John P. Schroeter (University of Texas Health Science Center at Houston)H-Index: 7
#2Steven J. Kolodziej (University of Texas Health Science Center at Houston)H-Index: 13
Last. James K. Stoops (University of Texas Health Science Center at Houston)H-Index: 24
view all 7 authors...
Abstract The three-dimensional structures of chymotrypsin- and methylamine-treated negatively stained human α 2 -macroglobulin have been determined by weighted back projection from electron microscope data. Projections of the reconstructions show good concordance with two-dimensional averages of both stained and frozen-hydrated molecules. The reconstructions reveal that the H-shaped front projection of the molecule is related to the smaller ellipsoidal end view by a rotation of 90° about the cro...
#1Charles T. Kresge (Mobil)H-Index: 19
#2Michael Leonowicz (Mobil)H-Index: 6
Last. J. S. BeckH-Index: 1
view all 5 authors...
MICROPOROUS and mesoporous inorganic solids (with pore diameters of ≤20 A and ∼20–500 A respectively)1 have found great utility as catalysts and sorption media because of their large internal surface area. Typical microporous materials are the crystalline framework solids, such as zeolites2, but the largest pore dimensions found so far are ∼10–12 A for some metallophosphates3–5 and ∼14 A for the mineral cacoxenite6. Examples of mesoporous solids include silicas7 and modified layered materials8–1...
#1Geoffrey A. Ozin (U of T: University of Toronto)H-Index: 119
#1Douglas F. Sticke (PSU: Pennsylvania State University)H-Index: 1
#2Leonard G. Presta (Genentech)H-Index: 36
Last. George D. Rose (UNC: University of North Carolina at Chapel Hill)H-Index: 60
view all 4 authors...
A global census of the hydrogen bonds in 42 X-ray-elucidated proteins was taken and the following demographic trends identified: (1) Most hydrogen bonds are local, i.e. between partners that are close in sequence, the primary exception being hydrogen-bonded ion pairs. (2) Most hydrogen bonds are between backbone atoms in the protein, an average of 68%. (3) All proteins studied have extensive hydrogen-bonded secondary structure, an average of 82%. (4) Almost all backbone hydrogen bonds are within...
#1Thomas W. Ebbesen (NEC)H-Index: 104
#2Pulickel M. Ajayan (NEC)H-Index: 191
INTEREST in carbon fibres1,2 has been stimulated greatly by the recent discovery of hollow graphitic tubules of nanometre dimensions3. There has been much speculation about the properties and potential application of these nanotubes4–8. Theoretical studies predict that their electronic properties will depend on their diameter and degree of helicity4,5. Experimental tests of these ideas has been hampered, however, by the lack of macroscopic quantities of the material. Here we report the synthesis...
1,2,4-triazin-5-one compounds of the general formula (I) (I) where R is are prepared by reacting a compound of general formula (II) (II) in which R is defined above with either (a) a tertiary alcohol of general formula (III) HO-R'(III) in which R' is a t-alkyl group having 4 to 18 carbon atoms, especially t-amyl or t-octyl or preferably t-butyl or (b) an alkene of general formula (IV) (IV) in which R1 and R2 are the same or different and are hydrogen or an alkyl group and R3 and R4 are the same ...
#1George M. Whitesides (Harvard University)H-Index: 271
#2John P. MathiasH-Index: 8
Last. Christopher T. SetoH-Index: 29
view all 3 authors...
Molecular self-assembly is the spontaneous association of molecules under equilibrium conditions into stable, structurally well-defined aggregates joined by noncovalent bonds. Molecular self-assembly is ubiquitous in biological systems and underlies the formation of a wide variety of complex biological structures. Understanding self-assembly and the associated noncovalent interactions that connect complementary interacting molecular surfaces in biological aggregates is a central concern in struc...
Cited By1398
#1Chenlei Wang (CAS: Chinese Academy of Sciences)
#2Linping Fu (CAS: Chinese Academy of Sciences)
Last. Yeteng Zhong (CAS: Chinese Academy of Sciences)H-Index: 23
view all 4 authors...
Peptide-based supramolecular self-assembly from peptide monomers into well-organized nanostructures, has attracted extensive attentions towards biomedical and biotechnological applications in recent decades. This spontaneous and reversible assembly process involving non-covalent bonding interactions can be artificially regulated. In this review, we have elaborated different strategies to modulate the peptide self-assembly through tuning the physicochemical and environmental conditions, including...
#1Alejandro Méndez‐Ardoy (University of Santiago de Compostela)H-Index: 4
#2Ignacio Insua (University of Santiago de Compostela)H-Index: 8
Last. Javier Montenegro (University of Santiago de Compostela)H-Index: 22
view all 4 authors...
Cyclic peptides are a fascinating class of molecules that can be programmed to fold or self-assemble into diverse mono- and multidimensional structures with potential applications in biomedicine, nanoelectronics, or catalysis. Herein we describe on-resin procedures to carry out head-to-tail peptide cyclization based on orthogonal protected linear structures. We also present essential characterization tools for obtaining dynamic and structural information, including the visualization cyclic pepti...
#1Yuhe Shen (TJU: Tianjin University)
#2Yuefei Wang (TJU: Tianjin University)H-Index: 15
Last. Zhimin He (TJU: Tianjin University)H-Index: 50
view all 6 authors...
Abstract null null Chirality is one of the most important structural features in biological systems. Peptides, as a class of small biomolecules, can self-assemble into various chiral supramolecular polymers with unprecedented levels of diversity and complexity, which have practical ramifications in various fields from catalysis to sensing, optics, and biomedicine. In this review, we will focus on the chiral transfer during peptide self-assembly from the molecular scale to the nano-, micro- and m...
#1Bárbara Claro (University of Porto)H-Index: 5
#2Antonio Peón (University of Porto)H-Index: 2
Last. Margarida M.S.M. Bastos (University of Porto)H-Index: 19
view all 8 authors...
Abstract null null Antimicrobial peptides are viewed as a promising alternative to conventional antibiotics, as their activity through membrane targeting makes them less prone to resistance development. Among them, antimicrobial D,L-α-cyclic peptides (CPs) have been proposed as an alternative, specially due to their cyclic nature and to the presence of D-α-amino acids that increases their resistance to proteases. In present work, second generation D,L-α-cyclic peptides with proven antimicrobial ...
#1Subhasish Roy (BGU: Ben-Gurion University of the Negev)H-Index: 16
#2Lianjun Zheng (Duke University)H-Index: 1
Last. Nurit Ashkenasy (BGU: Ben-Gurion University of the Negev)H-Index: 22
view all 9 authors...
Bioinspired peptide assemblies are promising candidates for use as proton-conducting materials in electrochemical devices and other advanced technologies. Progress toward applications requires establishing foundational structure-function relationships for transport in these materials. This experimental-theoretical study sheds light on how the molecular structure and proton conduction are linked in three synthetic cyclic peptide nanotube assemblies that comprise the three canonical basic amino ac...
#1Javid Ahmad Malla (Indian Institute of Science Education and Research, Pune)H-Index: 6
#2Manzoor Ahmad (Indian Institute of Science Education and Research, Pune)H-Index: 1
Last. Pinaki Talukdar (Indian Institute of Science Education and Research, Pune)H-Index: 25
view all 3 authors...
Self-assembly has become a powerful tool for building various supramolecular architectures with applications in material science, environmental science, and chemical biology. One such area is the development of artificial transmembrane ion channels that mimic naturally occurring channel-forming proteins to unveil various structural and functional aspects of these complex biological systems, hoping to replace the defective protein channels with these synthetically accessible moieties. This accoun...
#1Amutha Arul (SRM University)H-Index: 3
Last. Priyadip DasH-Index: 20
view all 9 authors...
#1Huong T. Kratochvil (UCSF: University of California, San Francisco)H-Index: 10
#2Robert W. Newberry (UCSF: University of California, San Francisco)H-Index: 15
Last. William F. DeGrado (UCSF: University of California, San Francisco)H-Index: 122
view all 5 authors...
Membrane-peptide interactions play critical roles in many cellular and organismic functions, including protection from infection, remodeling of membranes, signaling, and ion transport. Peptides interact with membranes in a variety of ways: some associate with membrane surfaces in either intrinsically disordered conformations or well-defined secondary structures. Peptides with sufficient hydrophobicity can also insert vertically as transmembrane monomers, and many associate further into membrane-...
#1Archana Gaurav (BHU: Banaras Hindu University)H-Index: 2
#2Vishal Sharma (BHU: Banaras Hindu University)H-Index: 2
Last. Ashish Kumar Tewari (BHU: Banaras Hindu University)H-Index: 14
view all 4 authors...
Abstract null null Here, we synthesize tripodal tweezer molecule which have cyanuric acid in the center, propylene as a linker and pthalimide hetrocycle as terminal for conformational applications. The propylene linker promote intramolecular and intermolecular interactions within and encircle molecules. Appropriately, the geometrical specification set for the molecules which must be concert about conformations in different states. The conformational studies of this tripodal compound has been car...
#1Yanqing Ge (China University of Petroleum)H-Index: 1
#2Chen Wang (China University of Petroleum)
Last. Jiqian Wang (China University of Petroleum)H-Index: 22
view all 6 authors...
To understand the molecular interaction mechanism and develop peptide-based hydrogels, a β-hairpin peptide CBHH was used as the model peptide, and its coassembly performance with succinic, malic, and tartaric dicarboxylates has been investigated with circular dichroism spectroscopy (CD) and atomic force microscopy (AFM). The rheological properties and cell culture performance of the coassembled hydrogels have also been assessed. The results showed that the dicarboxylates could induce the folding...
This website uses cookies.
We use cookies to improve your online experience. By continuing to use our website we assume you agree to the placement of these cookies.
To learn more, you can find in our Privacy Policy.