[Peptide nucleic acids and their phosphonate analogues: synthesis and hybridization characteristics].
The synthesis of a series of DNA mimics--peptide nucleic acids, phosphonate analogues of peptide nucleic acids, and their hybrids--is described. The preparative synthesis of the corresponding monomers and the solid phase automated synthesis of oligomers-mimics are developed. Modified phosphonate analogues of peptide nucleic acids, in particular chiral derivatives and those with additional hydroxyl groups in the side chains of the backbone as well as pyrene derivatives of peptide nucleic acids and their phosphonate analogues, are prepared. The ability of the resulting oligomers specifically to hybridize to DNA and RNA complementary chains is studied. It is shown that phosphonate analogues of peptide nucleic acids and their hybrids with peptide nucleic acids can form complexes with the DNA and RNA complementary strands, the stability of the complexes increasing in parallel with the increase in the number of peptide nucleic acid residues in the chain of the mimic. This property, along with good water solubility, provides the precondition for further evaluation of these compounds as antisense and antigene agents.
Efimov
V A
VA
Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia. eva@ibch.siobc.ras.ru
Buriakova
A A
AA
Chub
M B
MB
Chakhmakhcheva
O G
OG
D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000737:chemistry*; D018716:Molecular Mimicry; D009693:Nucleic Acid Hybridization; D063065:Organophosphonates / Q000737:chemistry*; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D012313:RNA / Q000737:chemistry
D063065:Organophosphonates; D020135:Peptide Nucleic Acids; D012313:RNA; D004247:DNA