Abstract
New polyanionic modifications of polyamide nucleic acid mimics were obtained. Thymine decamers were synthesized from respective chiral α- and γ-monomers, and their enantiomeric purity was assessed. Here, we present the decamer synthesis, purification and characterization by MALDI-TOF mass spectrometry and an investigation of the hybridization properties of the decamers. We show that the modified γ-S-carboxyethyl-T10 PNA forms a stable triplex with polyadenine DNA.
Highlights
Among the various agents that are capable of antigen- and antisense action [1], artificial biopolymers, peptide nucleic acids (PNAs) [2], occupy a special place
Because the stereochemical structure of chiral monomers in PNA oligomers impacts PNA binding with nucleic acid targets [9], we performed enantiomeric purity tests for the starting monomers 4 and 5 using direct and indirect chromatographic methods
This study demonstrates the first synthesis of three L-Glu-based polyanionic nucleic acid mimics
Summary
Among the various agents that are capable of antigen- and antisense action [1], artificial biopolymers, peptide nucleic acids (PNAs) [2], occupy a special place. A structural unit of PNAs is the N-(2-aminoethyl)-glycine (aeg) fragment with a nucleic heterocyclic base attached via the acetyl linker. This structure, on the one hand, allows an effective recognition of complementary sequences by nucleic bases [3] due to “restrained flexibility” [4] and, on the other hand, makes aeg-PNAs resistant to protease- and nuclease-mediated degradation due to non-natural bonds [5]. High sequence selectivity has been demonstrated for aeg-PNAs bases [3, 6], and this selectivity is markedly higher than that found for natural oligonucleotides and their analogues. Homopyrimidine aeg-PNAs are capable of insertion into dsDNA with ssDNA displacement [7]. Aeg-PNAs are capable of forming G-quadruplexes [8]
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