Themed collection Foldamers
Exploiting the interactions of aromatic units for folding and assembly in aqueous environments
A brief description of current models of aromatic interactions as well as a survey of aromatic foldamers in aqueous environments.
β-Peptide bundles: Design. Build. Analyze. Biosynthesize.
A perspective on the design and elaboration of β-peptide bundles, non-natural assemblies that exhibit many protein-like properties.
Remote control over folding by light
Integrating photoswitchable unit into helical macromolecules allows their conformations to be externally controlled by light and therefore provides a versatile strategy to design photoresponsive materials.
Towards vast libraries of scaffold-diverse, conformationally constrained oligomers
Protein ligands with high affinity and selectivity can be mined from large libraries of conformationally constrained oligomers.
Designing the structure and folding pathway of modular topological bionanostructures
Review of recent advances in the design of topologically folded (topofold) biomolecular nano-structures and their folding pathways.
Molecular switching involving metastable states: molecular thermal hysteresis and sensing of environmental changes by chiral helicene oligomeric foldamers
Molecular switching involving metastable states by chiral helicene oligomeric foldamers exhibits notable non-equilibrium thermodynamic properties, which can be used for sensing environmental changes.
Dynamic foldamer chemistry
Dynamic foldamers translate chemical signals into conformational changes, and hence into chemical outputs such as control of reactivity and selectivity.
Versatile ruthenium complexes based on 2,2′-bipyridine modified peptoids
Helical peptoids bearing 2,2′-bipyridine form ruthenium complexes via intermolecular binding to linear peptoid strands or intramolecular binding to a cyclic scaffold.
Electronic interactions of i, i + 1 dithioamides: increased fluorescence quenching and evidence for n-to-π* interactions
Adjacent thioamides can have electronic interactions that alter spectral properties and fluorescence quenching.
13-Helix folding of a β/γ-peptide manifold designed from a “minimal-constraint” blueprint
A bottom-up design rationale was used to select an alternating β/γ-peptide motif which folds into a well-defined 13-helix in solution.
Foldamer scaffolds suggest distinct structures are associated with alternative gains-of-function in a preamyloid toxin
An oligoquinoline foldamer library was synthesized and screened for agonism of lipid bilayer catalysed assembly of islet amyloid polypeptide (IAPP).
Stabilization of 11/9-helical α/β-peptide foldamers in protic solvents
A new cis-ACHC analogue, cis-2-amino-cis-4-methylcyclohexanecarboxylic acid, significantly stabilizes the 11/9-helix propensity in protic solvents.
Orthogonal strategy for the synthesis of dual-functionalised β3-peptide based hydrogels
We describe a new class of hydrogelator based on helical β3-peptide foldamers carrying a bioactive payload. The β3-peptides self-assemble to form a nanofibrous mesh resulting in a stable hydrogel. Co-incubation with different β3-peptide monomers allowed tuning of cell adherence.
An optimal hydrogen-bond surrogate for α-helices
The manuscript describes the impact of alkene-derived hydrogen bond isosteres on the stability of constrained helices.
Towards “bionic” proteins: replacement of continuous sequences from HIF-1α with proteomimetics to create functional p300 binding HIF-1α mimics
An extended sequence of α-amino acids in HIF-1α is replaced with a non-natural topographical mimic of an α-helix comprised from an aromatic oligoamide to reproduce its p300 recognition properties.
Small molecule-mediated duplex formation of nucleic acids with ‘incompatible’ backbones
A small molecule promotes duplex formation by nucleic acids with natural and non-natural backbones that otherwise do not form duplexes.
Unambiguous characterization of anisotropic foldamer packing in a foldecture with an elongated hexagonal plate shape
We report the first complete characterization of the directional molecular packing patterns of individual foldamers within a new foldecture with a well defined hexagonal plate shape.
Self-assembly of a 5-fluorouracil-dipeptide hydrogel
The self-assembly of 5-fluorouracil dilysine conjugates into self-supporting hydrogels, comprised of entangled nanofibers or rigid nanotubes with diameters of 10 and 16 nm, respectively, is reported.
Structure of a novel 13 nm dodecahedral nanocage assembled from a redesigned bacterial microcompartment shell protein
We report the crystal structure of a novel 60-subunit dodecahedral cage that results from self-assembly of a re-engineered version of a natural protein (PduA) from the Pdu microcompartment shell.
Structural features and molecular aggregations of designed triple-stranded β-sheets in single crystals
Design, synthesis, single-crystal conformations and molecular aggregations of hybrid triple-stranded β-sheets, and their structural analogy with protein structures are reported.
A nanofiber assembly directed by the non-classical antiparallel β-structure from 4S-(OH) proline polypeptide
The antiparallel arrangement of two strands of the non-classical β-structure, formed exclusively via cis-4S-(OH) prolyl polypeptide as established by FRET, propagates into self-assembled nanofibers upon conjugation with C12/C14/C16 hydrocarbon chains.
Structural studies of β-turn-containing peptide catalysts for atroposelective quinazolinone bromination
X-Ray crystallography and NMR spectroscopy were used to investigate the effect of primary structure on both secondary structure and enantioselectivity in peptide-based catalysts for an atroposelective bromination reaction.
X-ray structure of a lectin-bound DNA duplex containing an unnatural phenanthrenyl pair
DNA duplexes containing unnatural base-pair surrogates are attractive biomolecular nanomaterials with potentially beneficial photophysical or electronic properties.
Improved chemical and mechanical stability of peptoid nanosheets by photo-crosslinking the hydrophobic core
Photo-crosslinking produced more robust nanosheets that can survive sonication, lyophilization, and other biochemical manipulations.
Decorated self-assembling β3-tripeptide foldamers form cell adhesive scaffolds
β-Peptide foldamers were functionalised with the cell recognition motifs RGD or IKVAV, self-assembled into fibres, and co-assembled with non-functionalised β-peptides to yield tunable bioscaffolds with cell adhering properties.
Weak backbone CH⋯OC and side chain tBu⋯tBu London interactions help promote helix folding of achiral NtBu peptoids
The synthesis and helix folding propensity of achiral all-cis amide (NtBu)-glycine oligomers is reported.
Aryl-triazole foldamers incorporating a pyridinium motif for halide anion binding in aqueous media
Aryl-triazole foldamers incorporating a pyridinium motif are shown to be strongly halide anion binding in aqueous solvent mixtures.
Hairpin ribozyme mediated RNA recombination
An engineered hairpin ribozyme supports the recombination of two non-functional substrates into a functional hammerhead ribozyme.
Hydrogen bonding to carbonyl oxygen of nitrogen-pyramidalized amide – detection of pyramidalization direction preference by vibrational circular dichroism spectroscopy
Hydrogen-bonding to carbonyl of nitrogen-pyramidalized bicyclic β-proline amides can switch the preferred nitrogen-pyramidalization direction, as detected by VCD spectroscopy.
Citric acid encapsulation by a double helical foldamer in competitive solvents
Self-assembly combined with folding generate cavities for large polar guests.
Comparison of design strategies for α-helix backbone modification in a protein tertiary fold
Structural and thermodynamic analysis of a family of synthetic proteins with heterogeneous backbones yields new insights into the ability of unnatural amino acids to be accommodated into α-helices.
Folding-induced exciton coupling in homo- and heterodimers of merocyanine dyes
Folding of a bis(merocyanine) dye with two different chromophores leads to a model system to elucidate electronic interactions in heteroaggregates.
Surprising impact of remote groups on the folding–unfolding and dimer-chain equilibria of bifunctional H-bonding unimers
The remote end groups of aromatic foldamers are found to profoundly impact the assembling propensity of these molecules.
Modulation of helix stability of indolocarbazole–pyridine hybrid foldamers
The kinetic stabilities of the helical conformations of indolocarbazole–pyridine hybrid foldamers were modulated through single site modification.
Foldameric probes for membrane interactions by induced β-sheet folding
The adjustment of β-sheet content by β-amino acid substitutions revealed β-sheet folding-dependent biological activity.
Angiotensin II analogs comprised of Pro-Amb (γ-turn scaffold) as angiotensin II type 2 (AT2) receptor agonists
We describe herein the design, synthesis and conformational investigation of Pro-Amb (proline-3-amino-2-methoxybenzoic acid) incorporated Angiotensin II and its truncated analogues.
In situ iodination and X-ray crystal structure of a foldamer helix bundle
We report here the efficient in situ iodination of tyrosine-type side-chains located within a foldamer helix bundle, permitting structure determination using single-wavelength anomalous diffraction (SAD) methods.
Helix handedness inversion in arylamide foldamers: elucidation and free energy profile of a hopping mechanism
The free energy landscape and conformations of minima and intermediates along the stepwise handedness inversion pathway, proceeding through the simultaneous unfolding/folding of adjacent monomer–monomer linkages, for a helical arylamide foldamer.
Dynamic DNA architectures: spontaneous DNA strand exchange and self-sorting driven by perylene bisimide interactions
Three differently bay-substituted perylene bisimides together with the conventional unsubstituted chromophore were synthetically incorporated as homodimers in DNA double strands and undergo spontaneous strand exchange if mixed together.
The discovery of 9/8-ribbons, β/γ-peptides with curved shapes governed by a combined configuration-conformation code
The design of a β/γ-peptide reveals an unprecedented 9/8-ribbon whose curvature depends on the β-residue configuration and the γ-residue conformation.
About this collection
This themed collection, guest edited by Samuel Gellman and Ivan Huc, is a celebration of current achievements and future perspectives in the exciting field of Foldamers. It is a reflection of the breadth and the potential for development of the subject of folded artificial molecular architectures, covering peptidic foldamers, nucleic acid foldamers, abiotic oligomers, metallofoldamers, protein design and synthesis, folded polymers and their applications. New articles will be added to this collection as they are published.