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

doi:10.1016/j.tet.2010.10.056

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

10 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 language	English
Pages (from-to)	9659-9666
Number of pages	8
Journal	Tetrahedron
Volume	66
Issue number	51
DOIs	https://doi.org/10.1016/j.tet.2010.10.056
Publication status	Published - Dec 18 2010

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Keywords

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

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, 66(51), 9659-9666. https://doi.org/10.1016/j.tet.2010.10.056

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10.1016/j.tet.2010.10.056