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Synthesis and improved cross-linking properties of C5-modified furan bearing PNAs

(2017) MOLECULES. 22(11).
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Abstract
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 - or -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, -l-lysine and -l-arginine furan-PNA monomers were synthesized and incorporated in PNA sequences via solid phase synthesis. It was shown that the l-lysine -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 -modified PNA sequences towards single-stranded DNA.
Keywords
PNA, backbone modification, furan, crosslinking, chiral monomers, PEPTIDE NUCLEIC-ACIDS, DNA-BINDING, IN-VIVO, OLIGONUCLEOTIDE, RECOGNITION, EXPRESSION, CELLS, RNA, CONJUGATION, SELECTIVITY

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Citation

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Chicago
Elskens, Joke, Alex Manicardi, Valentina Costi, Annemieke Madder, and Roberto Corradini. 2017. “Synthesis and Improved Cross-linking Properties of C5-modified Furan Bearing PNAs.” Molecules 22 (11).
APA
Elskens, J., Manicardi, A., Costi, V., Madder, A., & Corradini, R. (2017). Synthesis and improved cross-linking properties of C5-modified furan bearing PNAs. MOLECULES, 22(11).
Vancouver
1.
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).
MLA
Elskens, Joke, Alex Manicardi, Valentina Costi, et al. “Synthesis and Improved Cross-linking Properties of C5-modified Furan Bearing PNAs.” MOLECULES 22.11 (2017): n. pag. Print.
@article{8541285,
  abstract     = {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 - or -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, -l-lysine and -l-arginine furan-PNA monomers were synthesized and incorporated in PNA sequences via solid phase synthesis. It was shown that the l-lysine -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 -modified PNA sequences towards single-stranded DNA.},
  articleno    = {2010},
  author       = {Elskens, Joke and Manicardi, Alex and Costi, Valentina and Madder, Annemieke and Corradini, Roberto},
  issn         = {1420-3049},
  journal      = {MOLECULES},
  language     = {eng},
  number       = {11},
  pages        = {20},
  title        = {Synthesis and improved cross-linking properties of C5-modified furan bearing PNAs},
  url          = {http://dx.doi.org/10.3390/molecules22112010},
  volume       = {22},
  year         = {2017},
}

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