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 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.
Harada
Hirotake
H
Department of Medical Genome Science, Graduate School of Frontier Sciences, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8562, Japan.
Funayama
Sho
S
Shoji
Yoshiaki
Y
Wada
Takeshi
T
D000409:Alanine / Q000737:chemistry; D002412:Cations / Q000737:chemistry; D004247:DNA / Q000737:chemistry; D009952:Ornithine / Q000737:chemistry; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D002412:Cations; D020135:Peptide Nucleic Acids; C051802:triplex DNA; D004247:DNA; D009952:Ornithine; D000409:Alanine