DNA‐Assisted Self‐Assembly of Pyrene Foldamers

• Published in: Chemistry : a European journal Vol. 15; no. 23; pp. 5701 - 5708
• Main Authors: Häner, Robert, Samain, Florent, Malinovskii, Vladimir L.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY‐VCH Verlag 02.06.2009
• Subjects: Base Sequence; Circular Dichroism; DNA; DNA - chemistry; double helix; excimer; Models, Molecular; Molecular Structure; Oligodeoxyribonucleotides - chemical synthesis; Oligodeoxyribonucleotides - chemistry; pyrene; Pyrenes - chemistry; self‐assembly; Spectrophotometry, Ultraviolet
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.200900369

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. 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.