Synthesis of two new thymine-containing negatively charged PNA monomers

Boyarskaya, N. P.; Kirillova, Yu. G.; Stotland, E. A.; Prokhorov, D. I.; Zvonkova, E. N.; Швец, В. И.

doi:10.1134/s0012500806050016

Cited by 13 publications

(11 citation statements)

References 8 publications

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“…The synthesis of the starting monomers 4 and 5 ( Fig 1C ) was performed using previously described methods [ 44 – 45 ], in which the key pseudopeptide intermediate was obtained via Mitsunobu condensation [ 46 ]. In a recent work, we reported the synthesis of monomer 4 via thymine alkylation with a bromoacetoamide precursor [ 47 ].…”

Section: Resultsmentioning

confidence: 99%

Polyanionic Carboxyethyl Peptide Nucleic Acids (ce-PNAs): Synthesis and DNA Binding

et al. 2015

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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.

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Section: Resultsmentioning

confidence: 99%

Polyanionic Carboxyethyl Peptide Nucleic Acids (ce-PNAs): Synthesis and DNA Binding

et al. 2015

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“…To investigate the effect of ionic strength on duplex stability for charged PNA, negatively and positively charged PNA monomers were synthesized using L-Asp [38] and L-Lys [17] residues, respectively, to construct the ethylenediamine portion of the PNA backbone (Figure 4). Substitution at the γ-position is known to be advantageous over substitution at the α-position, with regard to binding affinity, unambiguous antiparallel binding, and helical induction.…”

Section: Resultsmentioning

confidence: 99%

Evaluating the Effect of Ionic Strength on Duplex Stability for PNA Having Negatively or Positively Charged Side Chains

Costa

Heemstra

2013

PLoS ONE

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The enhanced thermodynamic stability of PNA:DNA and PNA:RNA duplexes compared with DNA:DNA and DNA:RNA duplexes has been attributed in part to the lack of electrostatic repulsion between the uncharged PNA backbone and negatively charged DNA or RNA backbone. However, there are no previously reported studies that systematically evaluate the effect of ionic strength on duplex stability for PNA having a charged backbone. Here we investigate the role of charge repulsion in PNA binding by synthesizing PNA strands having negatively or positively charged side chains, then measuring their duplex stability with DNA or RNA at varying salt concentrations. At low salt concentrations, positively charged PNA binds more strongly to DNA and RNA than does negatively charged PNA. However, at medium to high salt concentrations, this trend is reversed, and negatively charged PNA shows higher affinity for DNA and RNA than does positively charged PNA. These results show that charge screening by counterions in solution enables negatively charged side chains to be incorporated into the PNA backbone without reducing duplex stability with DNA and RNA. This research provides new insight into the role of electrostatics in PNA binding, and demonstrates that introduction of negatively charged side chains is not significantly detrimental to PNA binding affinity at physiological ionic strength. The ability to incorporate negative charge without sacrificing binding affinity is anticipated to enable the development of PNA therapeutics that take advantage of both the inherent benefits of PNA and the multitude of charge-based delivery technologies currently being developed for DNA and RNA.

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“…Their purity was evaluated by measuring their melting points which in all cases coincided with published data. The enantiomeric purity of amino alcohols IIa and IIb was determined from the optical rotation values which coincided with the data reported for analogous compounds prepared by reduction with borane in THF [7,11].…”

Section: Methodsmentioning

confidence: 99%

“…Amino dicarboxylic acids could give rise to trifunctional amino-, carboxy-, and hydroxy-containing chiral synthons with selectively removable protective groups, which can be used, e.g., for the preparation of monomers of negatively charged peptidonucleic acids [10,11].…”

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Preparative synthesis of β-amino alcohols from α-amino dicarboxylic acid derivatives

et al. 2009

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Synthesis of two new thymine-containing negatively charged PNA monomers

Cited by 13 publications

References 8 publications

Polyanionic Carboxyethyl Peptide Nucleic Acids (ce-PNAs): Synthesis and DNA Binding

Polyanionic Carboxyethyl Peptide Nucleic Acids (ce-PNAs): Synthesis and DNA Binding

Evaluating the Effect of Ionic Strength on Duplex Stability for PNA Having Negatively or Positively Charged Side Chains

Preparative synthesis of β-amino alcohols from α-amino dicarboxylic acid derivatives

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