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J Am Chem Soc. 2016 Aug 24;138(33):10522-30. doi: 10.1021/jacs.6b05063. Epub 2016 Aug 15.

Anatomy of an Oligourea Six-Helix Bundle.

Author information

1
Université de Bordeaux , CBMN, UMR 5248, Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac, France.
2
CNRS , CBMN, UMR 5248, 33600, Pessac, France.
3
CNRS , UMS3033/US001, Institut Européen de Chimie et Biologie, 33607 Pessac, France.
4
Université de Bordeaux , Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac, France.
5
Inserm , U1212, ARNA Laboratory, 146 rue Léo Saignat, 33076 Bordeaux, France.

Abstract

Non-natural synthetic oligomers that adopt well-defined secondary structures (i.e., foldamers) represent appealing components for the fabrication of bioinspired self-assembled architectures at the nanometer scale. Recently, peptidomimetic N,N'-linked oligourea helices have been designed de novo with the ability to fold into discrete helix bundles in aqueous conditions. In order to gain better insight into the determinants of oligourea helix bundle formation, we have investigated the sequence-to-structure relationship of an 11-mer oligourea previously shown to assemble into a six-helix bundle. Using circular dichroism, NMR spectroscopy, native mass-spectrometry and X-ray crystallography, we studied how bundle formation was affected by systematic replacement of the hydrophobic surface of the oligourea helix with either polar or different hydrophobic side chains. The molecular information gathered here has revealed several key requirements for foldamer bundle formation in aqueous conditions, and provides valuable insight toward the development of foldamer quaternary assemblies with improved (bio)physical properties and divergent topologies.

PMID:
27434817
DOI:
10.1021/jacs.6b05063

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