Oligopyrenotides: abiotic, polyanionic oligomers with nucleic acid-like structural properties.
Oligopyrenotides, abiotic oligomers that exhibit significant structural analogies to the nucleic acids, are described. They are composed of achiral, phosphodiester-linked pyrene building blocks and a single chiral 1,2-diaminocyclohexane unit. These oligomers form stable hybrids in aqueous solution. Hybridization is based on stacking interactions of the pyrene building blocks. They show thermal denaturation/renaturation behavior that closely resembles DNA and RNA hybridization. In addition, oligopyrenotides display salt-concentration-dependent structural polymorphism. Thus, they possess a number of structural attributes that are typical of nucleic acids and therefore may serve as model systems for the design of artificial self-replicating systems.
Häner
Robert
R
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland. robert.haener@ioc.unibe.ch
Garo
Florian
F
Wenger
Daniel
D
Malinovskii
Vladimir L
VL
D003514:Cyclohexylamines / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D009690:Nucleic Acid Conformation; D009693:Nucleic Acid Hybridization; D000071228:Polyelectrolytes; D011108:Polymers / Q000737:chemistry*; D011721:Pyrenes / Q000737:chemistry*
D003514:Cyclohexylamines; D004247:DNA; D000071228:Polyelectrolytes; D011108:Polymers; D011721:Pyrenes; C030984:pyrene; C030435:1,2-cyclohexanediamine