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Molecules 2017, 22(11), 2010;

Synthesis and Improved Cross-Linking Properties of C5-Modified Furan Bearing PNAs

Organic and Biomimetic Chemistry Research Group, Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281-S4, 9000 Gent, Belgium
Department of Chemistry, Life Sciences and Environmental Sustainability, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, Italy
These authors contributed equally to the work.
Authors to whom correspondence should be addressed.
Received: 21 October 2017 / Revised: 7 November 2017 / Accepted: 9 November 2017 / Published: 20 November 2017
(This article belongs to the Special Issue Molecular Properties and the Applications of Peptide Nucleic Acids)
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Over the past decades, peptide nucleic acid/DNA (PNA:DNA) duplex stability has been improved via backbone modification, often achieved via introducing an amino acid side chain at the α- or γ-position in the PNA sequence. It was previously shown that interstrand cross-linking can further enhance the binding event. In this work, we combined both strategies to fine-tune PNA crosslinking towards single stranded DNA sequences using a furan oxidation-based crosslinking method; for this purpose, γ-l-lysine and γ-l-arginine furan-PNA monomers were synthesized and incorporated in PNA sequences via solid phase synthesis. It was shown that the l-lysine γ-modification had a beneficial effect on crosslink efficiency due to pre-organization of the PNA helix and a favorable electrostatic interaction between the positively-charged lysine and the negatively-charged DNA backbone. Moreover, the crosslink yield could be optimized by carefully choosing the type of furan PNA monomer. This work is the first to describe a selective and biocompatible furan crosslinking strategy for crosslinking of γ-modified PNA sequences towards single-stranded DNA. View Full-Text
Keywords: PNA; backbone modification; furan; crosslinking; chiral monomers PNA; backbone modification; furan; crosslinking; chiral monomers

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Elskens, J.; Manicardi, A.; Costi, V.; Madder, A.; Corradini, R. Synthesis and Improved Cross-Linking Properties of C5-Modified Furan Bearing PNAs. Molecules 2017, 22, 2010.

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