Synthesis and Improved Cross-Linking Properties of C5-Modified Furan Bearing PNAs
AbstractOver 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
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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.
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(11):2010.Chicago/Turabian Style
Elskens, Joke; Manicardi, Alex; Costi, Valentina; Madder, Annemieke; Corradini, Roberto. 2017. "Synthesis and Improved Cross-Linking Properties of C5-Modified Furan Bearing PNAs." Molecules 22, no. 11: 2010.
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