High‐Affinity Hybridization of Complementary Aromatic Oligoamide Strands in Water

Author:

Koehler Victor1,Bruschera Gabrielle1,Merlet Eric1,Mandal Pradeep K.2ORCID,Morvan Estelle3,Rosu Frédéric3ORCID,Douat Céline2,Fischer Lucile1,Huc Ivan2ORCID,Ferrand Yann1ORCID

Affiliation:

1. CBMN (UMR 5248) Univ. Bordeaux CNRS Bordeaux Institut National Polytechnique 2 rue Escarpit 33600 Pessac France

2. Department Pharmazie Ludwig-Maximilians-Universität München Butenandtstr. 5–13 81377 München Germany

3. IECB UAR3033 Univ. ćBordeaux CNRS INSERM 2 rue Robert Escarpit 33600 Pessac France

Abstract

AbstractWe prepared a series of water‐soluble aromatic oligoamide sequences all composed of a segment prone to form a single helix and a segment prone to dimerize into a double helix. These sequences exclusively assemble as antiparallel duplexes. The modification of the duplex inner rim by varying the nature of the substituents borne by the aromatic monomers allowed us to identify sequences that can hybridize by combining two chemically different strands, with high affinity and complete selectivity in water. X‐ray crystallography confirmed the expected antiparallel configuration of the duplexes whereas NMR spectroscopy and mass spectrometry allowed us to assess precisely the extent of the hybridization. The hybridization kinetics of the aromatic strands was shown to depend on both the nature of the substituents responsible for strand complementarity and the length of the aromatic strand. These results highlight the great potential of aromatic hetero‐duplex as a tool to construct non‐symmetrical dynamic supramolecular assemblies.

Publisher

Wiley

Subject

General Chemistry,Catalysis

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