Issue 93, 2015

Solvent assisted structural diversity: supramolecular sheet and double helix of a short aromatic γ-peptide

Abstract

Solvent interaction has a significant effect on the folding and structural diversity of short aromatic γ-peptides that lead to a change in initial helical conformation. The internal rigidity of building blocks promotes the helical conformations of the γ-peptides containing m-aminobenzoic acid and N, N′-dicyclohexylurea. Various solution state NMR experiments show the existence of intermolecular hydrogen bonded structures of the short aromatic γ-peptides. In a polar protic solvent (MeOH), the helical strand interacts with the solvent molecules and expands to a more open (nearly extended) structure which further self-assembles to form a supramolecular sheet like structure. However, crystals obtained from chloroform show a supramolecular double helix which is stabilized by intermolecular hydrogen bonding and π–π stacking interactions. The report describes how significantly different self-assembled structures are developed from compounds folded in a subtly different manner by interaction with the solvent.

Graphical abstract: Solvent assisted structural diversity: supramolecular sheet and double helix of a short aromatic γ-peptide

Supplementary files

Article information

Article type
Paper
Submitted
02 Jul 2015
Accepted
01 Sep 2015
First published
01 Sep 2015

RSC Adv., 2015,5, 76257-76262

Solvent assisted structural diversity: supramolecular sheet and double helix of a short aromatic γ-peptide

R. Sarkar, M. Debnath, K. Maji and D. Haldar, RSC Adv., 2015, 5, 76257 DOI: 10.1039/C5RA12831E

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