Duplex Foldamers from Assembly Induced Folding

Abstract

Oligoamide strands 1, 2, and 3, consisting of 4-H-bond units, were originally designed to form noncovalent polymers based on the expectation that they would adopt an extended conformation. Instead of assembling into the expected supramolecular polymer through their 4-H-bond units, the 1:1 mixture of 1 and 2 was found to form a highly stable dimeric species. To dimerize, the H-bonding sequences of 1 and 2 can only adopt a folded (stacked) conformation. The self-assembly of 3 was also found to adopt a similar folded duplex conformation. These novel duplex foldamers are very stable. They were characterized by 1D and 2D 1H NMR, VPO, and mass spectral (ESI) studies.

Surprising impact of remote groups on the folding–unfolding and dimer-chain equilibria of bifunctional H-bonding unimers

“…In our previous study, 10 examining the assembly of 1 and that of another analogous pair of oligoamide strands having different 4-H-bonded units revealed a surprising outcome. Instead of forming extended polymeric aggregates, compound 1 and its analogs formed H-bonded dimers, which we dubbed “duplex foldamers”, in which the component oligoamide strands folded into a conformation that (Fig.…”

“…10 Compound 1 , consisting of two unsymmetrical 4-H-bonded units 11,12 covalently linked in a head-to-head fashion, represents one such design of this series. If adopting an extended conformation, a molecule of 1 could only partially overlap with another one via four intermolecular H-bonds, and would thus lead to linear H-bonded polymers.…”

Polymerization of methyl methacrylate with a thermal iniferter: Diethyl 2,3‐dicyano‐2,3‐di(p‐tolyl)succinate

“…The model compounds 1 and 2 (Fig. 1) chosen for the experiments were designed and synthesized by previous methods 25, 26, 32, 33. The coupling reactions were carried out by the standard peptide coupling methods and the resulting oligoamides contain 1,3‐disubstituted benzene rings linked by α‐amino acid residues containing a variety of sequences using H‐bonding donor (D) and acceptor (A) sites, i.e.…”

Preliminary mechanistic information on disulfide‐bond formation and the role of hydrogen bonds by nanoelectrospray mass spectrometry

“…1) chosen for the experiments were designed and synthesized by previous methods. 25,26,32,33 The coupling reactions were carried out by the standard peptide coupling methods and the resulting oligoamides contain 1,3-disubstituted benzene rings linked by˛-amino acid residues containing a variety of sequences using H-bonding donor (D) and acceptor (A) sites, i.e. amide O and H atoms.…”