Supramolecular structures involving peptide nucleic acid.

摘要

This thesis work extends the body of knowledge on the properties of PNA/PNA and PNA/DNA duplexes into a perspective of material science and supramolecular chemistry.; Chapter I includes a detailed introduction to peptide nucleic acid and the structural analogs of PNA. A background information on the ligand-nucleic acid interactions is provided.; Chapter II covers the synthesis of backbone-modified chiral PNAs and the use of modified PNA/DNA duplexes as templates for the assembly of organic dye molecules (DiSC₂(5)). This specific dye constitutes the first example of the ligand binding to mixed sequence PNA-containing hybrids. Moreover, thermodynamics and hybridization properties of modified PNA/DNA duplexes are investigated and the structural modifications on PNA/DNA duplexes are confirmed by a summarized collaborative study. Chapter III expands the formation of supramolecular structures by dye aggregates on PNA/PNA duplexes. The electrostatic contribution to the dye assembly on PNA/PNA duplexes are investigated along with a deeper discussion of PNA-ligand interactions.; Chapter IV explores the use of both backbone- and nucleobase-modified PNA/PNA duplexes in a lipid environment, presenting implications for a transmembrane supramolecular architecture involving PNA.; Finally, in Chapter V, a PNA/PNA duplex is modified at the end termini with organic donor and acceptor groups to be exploited as a model system for future charge/electron transfer studies utilizing PNA as a medium of transfer.