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Supramolecular Self‐Assembly of β 3 ‐Peptides Mediated by Janus‐Type Recognition Units
Author(s) -
Kabatas Glowacki Selda,
Koszinowski Konrad,
Hübner Dennis,
Frauendorf Holm,
Vana Philipp,
Diederichsen Ulf
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202003107
Subject(s) - supramolecular chemistry , circular dichroism , chemistry , molecular recognition , folding (dsp implementation) , stacking , electrospray ionization , rational design , intramolecular force , peptide , crystallography , supramolecular assembly , helix (gastropod) , hydrogen bond , stereochemistry , molecule , nanotechnology , mass spectrometry , materials science , biochemistry , organic chemistry , biology , ecology , chromatography , snail , electrical engineering , engineering
Abstract To gain mechanistic insights, natural systems with biochemical relevance are inspiring for the creation of new biomimetics with unique properties and functions. Despite progress in rational design and protein engineering, folding and intramolecular organization of individual components into supramolecular structures remains challenging and requires controlled methods. Foldamers, such as β‐peptides, are structurally well defined with rigid conformations and suitable for the specific arrangement of recognition units. Herein, we show the molecular arrangement and aggregation of β 3 ‐peptides into a hexameric helix bundle. For this purpose, β‐amino acid side chains were modified with cyanuric acid and triamino‐ s ‐triazine as complementary recognition units. The pre‐organization of the β 3 ‐peptides leads these Janus molecule pairs into a hexameric arrangement and a defined rosette nanotube by stacking. The helical conformation of the subunits was indicated by circular dichroism spectroscopy, while the supramolecular arrangement was detected by dynamic light scattering and confirmed by high‐resolution electrospray ionization mass spectrometry (ESI‐HRMS).