Solid-phase synthesis and properties of chiral peptide nucleic acids bearing cationic side chains

A novel chiral peptide nucleic acid, ornithine-based nucleobase-linked polyamide (ONA), aimed to hybrid with a DNA duplex to form triplexes, was designed and synthesized. The chiral monomers composed of the ornithine-based backbone and the serine-derived side chains were synthesized in stereocontrol...

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Bibliographic Details
Published in:Nucleic Acids Symposium Series 2007-11, Vol.51 (1), p.259-260
Main Authors: Harada, Hirotake, Funayama, Sho, Shoji, Yoshiaki, Wada, Takeshi
Format: Article
Language:English
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Summary:A novel chiral peptide nucleic acid, ornithine-based nucleobase-linked polyamide (ONA), aimed to hybrid with a DNA duplex to form triplexes, was designed and synthesized. The chiral monomers composed of the ornithine-based backbone and the serine-derived side chains were synthesized in stereocontrolled manners. The diastereopure oligomers were synthesized by a solid-phase method using the diastereopure monomers. Highly cross-linked polystyrene (HCP) resin was employed as a solid support to minimize the aggregation of the oligomer which was suspected to occur during the chain elongation. By the use of new solid-phase method, homo-thymine ONA oligomers were synthesized in good yields. The ONA hexamer was found to form a triplex with the dsDNA in a sequence specific manner.
ISSN:0261-3166
1746-8272
DOI:10.1093/nass/nrm130