Synthesis of pyrrolidine-based oxy-peptide nucleic acids carrying four types of nucleobases and their transport into cytoplasm

Mizuki Kitamatsu, Akiko Takahashi, Takashi Ohtsuki, Masahiko Sisido

Research output: Contribution to journal › Article

9 Citations (Scopus)

Abstract

We synthesized 16 pyrrolidine-based oxy-peptide nucleic acid (POPNA) monomers carrying four different nucleobases onto four different stereoisomers of pyrrolidine rings. Using these monomers, we prepared POPNA oligomers, which formed sequence-specific hybrids with DNAs. The oligomer configurations influenced the hybrid stability. The oligomers were not taken into CHO cells. However, they could enter the cell cytoplasm when mixed with the influenza virus hemagglutinin peptide-arginine heptamer conjugate.

Original languageEnglish
Pages (from-to)9659-9666
Number of pages8
JournalTetrahedron
Volume66
Issue number51
DOIs
Publication statusPublished - Dec 18 2010

Fingerprint

Peptide Nucleic Acids
Oligomers
Cytoplasm
Monomers
Stereoisomerism
CHO Cells
Hemagglutinins
Orthomyxoviridae
Viruses
Arginine
Peptides
DNA
pyrrolidine

Keywords

  • Cell-penetrating peptide
  • Confocal laser scanning microscopy
  • Peptide nucleic acid
  • Solid-phase peptide synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of pyrrolidine-based oxy-peptide nucleic acids carrying four types of nucleobases and their transport into cytoplasm. / Kitamatsu, Mizuki; Takahashi, Akiko; Ohtsuki, Takashi; Sisido, Masahiko.

In: Tetrahedron, Vol. 66, No. 51, 18.12.2010, p. 9659-9666.

Research output: Contribution to journal › Article

Kitamatsu, M, Takahashi, A, Ohtsuki, T & Sisido, M 2010, 'Synthesis of pyrrolidine-based oxy-peptide nucleic acids carrying four types of nucleobases and their transport into cytoplasm', Tetrahedron, vol. 66, no. 51, pp. 9659-9666. https://doi.org/10.1016/j.tet.2010.10.056
Kitamatsu M, Takahashi A, Ohtsuki T, Sisido M. Synthesis of pyrrolidine-based oxy-peptide nucleic acids carrying four types of nucleobases and their transport into cytoplasm. Tetrahedron. 2010 Dec 18;66(51):9659-9666. https://doi.org/10.1016/j.tet.2010.10.056
Kitamatsu, Mizuki ; Takahashi, Akiko ; Ohtsuki, Takashi ; Sisido, Masahiko. / Synthesis of pyrrolidine-based oxy-peptide nucleic acids carrying four types of nucleobases and their transport into cytoplasm. In: Tetrahedron. 2010 ; Vol. 66, No. 51. pp. 9659-9666.
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