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

Yuliya Kirillova; Nataliya Boyarskaya; Andrey Dezhenkov; Mariya Tankevich; Ivan Prokhorov; Anna Varizhuk; Sergei Eremin; Dmitry Esipov; Igor Smirnov; Galina Pozmogova

doi:10.1371/journal.pone.0140468

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

PLoS One. 2015 Oct 15;10(10):e0140468. doi: 10.1371/journal.pone.0140468. eCollection 2015.

Authors

Affiliations

¹ Department of Biotechnology and Bionanotechnology, Moscow State University of Fine Chemical Technologies, Moscow, Russia; Department of Molecular Biology and Genetics, SRI of Physical-Chemical Medicine, Moscow, Russia.
² Department of Biotechnology and Bionanotechnology, Moscow State University of Fine Chemical Technologies, Moscow, Russia.
³ Department of Molecular Biology and Genetics, SRI of Physical-Chemical Medicine, Moscow, Russia; Department of Structure-Functional Analysis of Biopolymers, Engelhardt Institute of Molecular Biology, Moscow, Russia.
⁴ Department of Bioorganic Chemistry, Biology Faculty, Moscow State University, Moscow, Russia.
⁵ Department of Molecular Biology and Genetics, SRI of Physical-Chemical Medicine, Moscow, Russia.

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

DNA / chemical synthesis*
DNA / chemistry
Nylons / chemistry
Oligonucleotides / chemical synthesis*
Oligonucleotides / chemistry
Peptides / chemistry*
Polyelectrolytes
Polymers / chemistry*

Substances

Nylons
Oligonucleotides
Peptides
Polyelectrolytes
Polymers
polyanions
DNA

Grants and funding

This work was supported by Russian Science Foundation [14-25-00013, GP] URL: (http://www.rscf.ru) and Russian Foundation for Basic Research (in part) [14-04-01244, AV] URL: (http://www.rfbr.ru/rffi/ru). The funders had no role in study design, data collection and analysis, decision to publish, or preparation of the manuscript.