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DNA‐Assisted Self‐Assembly of Pyrene Foldamers
Author(s) -
Häner Robert,
Samain Florent,
Malinovskii Vladimir L.
Publication year - 2009
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.200900369
Subject(s) - pyrene , chemistry , stacking , dna , molecule , crystallography , circular dichroism , stereochemistry , helix (gastropod) , organic chemistry , biochemistry , ecology , snail , biology
Folding in the tides : Upon hybridization, pyrene molecules assemble through interstrand stacking interactions to form double‐stranded, helical structures. Structural organization of the pyrene molecules is an intrinsic property of the oligoaryl part and takes place independently of the sequence of the attached DNA. Pyrene helicity is most pronounced in a bi‐segmental chimera, in which a DNA stem is present only at one end of the pyrene section.The self‐organization of oligopyrene foldamers is described. Bi‐ and tri‐segmental oligomers composed of nucleotides and non‐nucleosidic, achiral pyrene monomers form double‐stranded helical structures, as shown by absorbance, fluorescence, and CD spectroscopy. The mixed nature of alternating aromatic and phosphate groups ensures water solubility which, in turn, favors folding of the aromatic units. Pyrene molecules also assemble though interstrand stacking interactions. Structural organization of the pyrene units is an intrinsic property of the oligoaryl part and takes place independently from the sequence of the attached DNA. Chirality transfer from DNA to the pyrene segment leads to formation of a double helix, in which neighboring pyrene units are, in the present case, twisted in a right‐handed manner. Pyrene helicity is most pronounced in a bi‐segmental chimera, in which a DNA stem is present only at one end of the pyrene section.