Synthesis and properties of PNA containing a dicationic nucleobase based on N 4 -benzoylated cytosine

We report the synthesis of a peptide nucleic acid (PNA) monomer containing N -bis(aminomethyl)benzoylated cytosine ( C base). The C monomer was incorporated into PNA oligomers using Fmoc-based solid-phase synthesis. The C base in PNA had two positive charges and exhibited greater affinity for DNA G...

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Bibliographic Details
Published inBioorganic & medicinal chemistry letters Vol. 88; p. 129287
Main Authors Moriya, Shun-Suke, Funaki, Kaoru, Demizu, Yosuke, Kurihara, Masaaki, Kittaka, Atsushi, Sugiyama, Toru
Format Journal Article
LanguageEnglish
Published England 15.05.2023
Subjects
Cytosine
DNA - chemistry
Peptide Nucleic Acids - chemistry
Strand invasion
Antigene
Peptide nucleic acid
Positive charge
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Summary:We report the synthesis of a peptide nucleic acid (PNA) monomer containing N -bis(aminomethyl)benzoylated cytosine ( C base). The C monomer was incorporated into PNA oligomers using Fmoc-based solid-phase synthesis. The C base in PNA had two positive charges and exhibited greater affinity for DNA G base than the natural C base. The C base stabilized PNA-DNA heteroduplexes through electrostatic attractions, even in high salt conditions. The two positive charges on the C residue did not compromise the sequence specificity of PNA oligomers. These insights will aid the future design of cationic nucleobases.
ISSN:1464-3405