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Sequence-specific and Selective Recognition of Double-stranded RNAs over Single-stranded RNAs by Chemically Modified Peptide Nucleic Acids
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PNA monomers fully compatible with standard Fmoc-based solid-phase synthesis of pseudocomplementary PNA.

Toru Sugiyama1, Genki Hasegawa1, Chie Niikura1

  • 1Faculty of Pharmaceutical Sciences, Teikyo University, Itabashi-ku, Tokyo 173-8605, Japan.

Bioorganic & Medicinal Chemistry Letters
|June 15, 2017
PubMed
Summary

Researchers developed new peptide nucleic acid (PNA) monomers for pseudocomplementary PNA (pcPNA) synthesis. These monomers are compatible with Fmoc chemistry, enabling easier creation of PNA oligomers for diverse applications.

Keywords:
AntigenePeptide nucleic acidPseudocomplementaryStrand invasion

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Area of Science:

  • Synthetic organic chemistry
  • Biochemistry
  • Molecular biology

Background:

  • Peptide nucleic acids (PNAs) are DNA/RNA mimics with unique binding properties.
  • Standard PNA synthesis faces challenges with specific monomer compatibility.
  • Pseudocomplementary PNA (pcPNA) offers enhanced specificity in molecular interactions.

Purpose of the Study:

  • To synthesize novel PNA monomers for pseudocomplementary PNA (pcPNA).
  • To ensure compatibility of new monomers with standard Fmoc solid-phase synthesis.
  • To facilitate broader applications of PNA in biotechnology and medicine.

Main Methods:

  • Protection of 2-thiouracil (sU) with 4-methoxy-2-methybenzyl (MMPM) group.
  • Protection of diaminopurine (D) exocyclic amino groups with Boc groups.
  • Incorporation of novel monomers into a 10-mer PNA oligomer via Fmoc chemistry.

Main Results:

  • Successful synthesis of new PNA monomers compatible with Fmoc chemistry.
  • Smooth incorporation of monomers during solid-phase oligomerization.
  • HPLC and MALDI-TOF MS confirmed complete removal of the MMPM protecting group from sU.

Conclusions:

  • The developed PNA monomers are fully compatible with standard Fmoc chemistry.
  • These monomers simplify the synthesis of pcPNA oligomers.
  • The new monomers will advance PNA applications in antigene strategies and DNA nanotechnology.