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Themed collection Foldamer Chemistry

21 items
Communication

Intramolecular chiral communication in peptide–dendron hybrids

Intramolecular chirality transfer, amplification and solvent-mediated switching was observed in a series of random-coil peptide–dendron hybrids.

Graphical abstract: Intramolecular chiral communication in peptide–dendron hybrids
From the themed collection: Foldamer Chemistry
Communication

Self-association-driven transition of the β-peptidic H12 helix to the H18 helix

Foldamer sequences constructed by using trans-ABHC and β3-hSer residues produce β-H18 helix in a solvent- and concentration-dependent way.

Graphical abstract: Self-association-driven transition of the β-peptidic H12 helix to the H18 helix
From the themed collection: Foldamer Chemistry
Communication

Z-Formamidoximes in molecular folding and macrocycles

The formamidoxime Z isomer coupled with the pyridylbiscarboxamide conformational codon fold into planar, curved units prone to self-assembly into channel-like structures, as examplified with original macrocycles.

Graphical abstract: Z-Formamidoximes in molecular folding and macrocycles
From the themed collection: Foldamer Chemistry
Paper

ortho-Phenylene oligomers with terminal push–pull substitution

Substituent effects on conformational behavior and electronic spectra have been examined in the first series of push–pull o-phenylenes.

Graphical abstract: ortho-Phenylene oligomers with terminal push–pull substitution
From the themed collection: Foldamer Chemistry
Paper

Novel peptide foldameric motifs: a step forward in our understanding of the fully-extended conformation/310-helix coexistence

Fluorescent PyrAc-(Deg)n-O-(pNO2)Bzl peptides exist as mixtures of fully-extended (right) and 310-helical conformers, the latter typical of (Aib)n oligomers.

Graphical abstract: Novel peptide foldameric motifs: a step forward in our understanding of the fully-extended conformation/310-helix coexistence
From the themed collection: Foldamer Chemistry
Paper

Expedient synthesis of pseudo-Pro-containing peptides: towards constrained peptidomimetics and foldamers

The reaction of sulfonyl peptides containing L- or D-configured Ser or Thr with bis(succinimidyl) carbonate in the presence of a catalytic amount of a base affords, in solution or in the solid phase, the corresponding peptides with one or two, consecutive or alternate oxazolidin-2-ones (Oxd).

Graphical abstract: Expedient synthesis of pseudo-Pro-containing peptides: towards constrained peptidomimetics and foldamers
From the themed collection: Foldamer Chemistry
Paper

Solid state NMR studies of oligourea foldamers: Interaction of 15N-labelled amphiphilic helices with oriented lipid membranes

The 15N-chemical shift tensor of urea bonds is determined and the bilayer topology of an antimicrobial oligourea analysed.

Graphical abstract: Solid state NMR studies of oligourea foldamers: Interaction of 15N-labelled amphiphilic helices with oriented lipid membranes
From the themed collection: Foldamer Chemistry
Paper

Conformational stability of collagen triple helices functionalized in the Yaa position by click chemistry

Click chemistry was used to introduce moieties as sterically demanding as monosaccharides into the Yaa position of collagen model peptides. The effect of different triazolyl derivatives as well as the configuration of the functionalized proline residue on the thermal stability of the collagen triple helices was examined.

Graphical abstract: Conformational stability of collagen triple helices functionalized in the Yaa position by click chemistry
From the themed collection: Foldamer Chemistry
Paper

Trichogin GA IV: A versatile template for the synthesis of novel peptaibiotics

One or more Gly-to-Lys replacements on the hydrophilic face of the peptide-template trichogin GA IV modulate its biological properties and promote a pH-mediated, reversible, 310- to α-helix transition.

Graphical abstract: Trichogin GA IV: A versatile template for the synthesis of novel peptaibiotics
From the themed collection: Foldamer Chemistry
Paper

Synthesis, structural investigation and computational modelling of water-binding aquafoldamers

A series of water-binding aquafoldamers have been studied in detail, illustrating their potential use for recognizing larger water clusters of diverse topologies and as synthetic water channels.

Graphical abstract: Synthesis, structural investigation and computational modelling of water-binding aquafoldamers
From the themed collection: Foldamer Chemistry
Paper

Conformational stability studies of a stapled hexa-β3-peptide library

An extensive library of new, 14-helical, hexa β3-peptides demonstrates that appropriately stapled hexa-β3-peptides can allow for a number of variations, including staple size, location and functionalization, without significant perturbation of the 14-helix.

Graphical abstract: Conformational stability studies of a stapled hexa-β3-peptide library
From the themed collection: Foldamer Chemistry
Paper

Designing hybrid foldamers: the effect on the peptide conformational bias of β- versus α- and γ-linear residues in alternation with (1R,2S)-2-aminocyclobutane-1-carboxylic acid

Conformational bias can be tuned from ribbon-type structures to β-sheet-like and helical motifs by intercalating suitable linear segments between cis-cyclobutane residues

Graphical abstract: Designing hybrid foldamers: the effect on the peptide conformational bias of β- versus α- and γ-linear residues in alternation with (1R,2S)-2-aminocyclobutane-1-carboxylic acid
From the themed collection: Foldamer Chemistry
Paper

Effect of capping groups at the N- and C-termini on the conformational preference of α,β-peptoids

Different capping groups have significant effects on spectral features/conformation of α,β-peptoids by CD, IR and NMR. These are most pronounced for shorter oligomers and are solvent dependent. This underlines the importance of considering capping groups for conformational studies.

Graphical abstract: Effect of capping groups at the N- and C-termini on the conformational preference of α,β-peptoids
From the themed collection: Foldamer Chemistry
Paper

β-Phenylproline: the high β-turn forming propensity of proline combined with an aromatic side chain

The β-phenyl group attached to proline does not disrupt the β-turn propensity of the natural amino acid.

Graphical abstract: β-Phenylproline: the high β-turn forming propensity of proline combined with an aromatic side chain
From the themed collection: Foldamer Chemistry
Paper

Flexible oligocholate foldamers as membrane transporters and their guest-dependent transport mechanism

Flexible oligocholate foldamers transport carboxyfluorescein and glucose across lipid membranes in distinctively different mechanisms.

Graphical abstract: Flexible oligocholate foldamers as membrane transporters and their guest-dependent transport mechanism
From the themed collection: Foldamer Chemistry
Paper

Design and synthesis of trans-3-aminopyran-2-carboxylic acid (APyC) and α/β-peptides with 9/11-helix

The participation of pyran oxygen of trans-3-aminopyran-2-carboxylic acid (APyC) in α/β-peptides resulting in 9/11-helix is envisaged to provide scope for new designs.

Graphical abstract: Design and synthesis of trans-3-aminopyran-2-carboxylic acid (APyC) and α/β-peptides with 9/11-helix
From the themed collection: Foldamer Chemistry
Paper

meta-Substituted benzamide oligomers that complex mono-, di- and tricarboxylates: folding-induced selectivity and chirality

Benzamide-derived oligomers fold into compact conformations to complex aromatic and aliphatic carboxylate anions though multiple intermolecular N–H⋯O and C–H⋯O hydrogen bonds, and display helical chirality upon binding chiral glutamic acid dianion.

Graphical abstract: meta-Substituted benzamide oligomers that complex mono-, di- and tricarboxylates: folding-induced selectivity and chirality
From the themed collection: Foldamer Chemistry
Paper

Stereoselective preparation of β,γ-methano-GABA derivatives

The Kulinkovich–de Meijere reaction provides non-racemic trans cyclopropylamines, which are converted into enantiomerically pure N-Boc protected β,γ-methano-GABA derivatives.

Graphical abstract: Stereoselective preparation of β,γ-methano-GABA derivatives
From the themed collection: Foldamer Chemistry
Paper

Synthesis of novel β-aminocyclobutanecarboxylic acid derivatives by a solvent-free aza–Michael addition and subsequent ring closure

A solvent-free aza–Michael addition leading to new substituted β-aminocyclobutanecarboxylic acid derivatives and the reactivity of these donor–acceptor substituted cyclobutanes is described.

Graphical abstract: Synthesis of novel β-aminocyclobutanecarboxylic acid derivatives by a solvent-free aza–Michael addition and subsequent ring closure
From the themed collection: Foldamer Chemistry
Paper

The interaction of lipid modified pseudopeptides with lipid membranes

The conformational preferences of two lipopeptides Cn2H(2n+1)CO-L-Phe-D-Oxd-OBn or Cn2H(2n+1)CO-D-Phe-L-Oxd-OBn with n = 5 or 11 have been analyzed with solid-state 2H and 13C NMR techniques.

Graphical abstract: The interaction of lipid modified pseudopeptides with lipid membranes
From the themed collection: Foldamer Chemistry
Paper

Regio- and diastereoselective fluorination of alicyclic β-amino acids

Regio- and stereoselective approaches to fluorinated alicyclic β-amino esters has been developed.

Graphical abstract: Regio- and diastereoselective fluorination of alicyclic β-amino acids
From the themed collection: Foldamer Chemistry
21 items

About this collection

The peer-reviewed articles in this Organic & Biomolecular Chemistry's web theme issue highlight recent cutting-edge achievements in the exciting frontier field of Foldamer Chemistry.

The guest editor of this issue is Professor Ferenc Fulop (University of Szeged, Hungary). We hope that you will find this collection of articles enjoyable and interesting to read. Why not also view Professor Fulop's introduction to the web theme issue, available on our blog?

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