Synthesis of C-nucleoside analogues based on the pyrimidine skeleton for the formation of anti-parallel-type triplex DNA with a CG mismatch site

Ryotaro Notomi, Lei Wang, Takayuki Osuki, Hidenori Okamura, Shigeki Sasaki, Yosuke Taniguchi

Research output: Contribution to journalArticlepeer-review

Abstract

The triplex DNA forming method is an attractive tool as a gene-targeting agent. Using artificial nucleoside analogues based on C-nucleoside, stable and selective triplex DNA can be formed in a specific region of duplex DNA, and its biotechnology applications will greatly expand. In this study, we designed and synthesized novel C-nucleoside analogues based on the pyrimidine skeleton, 3MeAP-d(Y-Cl) and 3MeAP-d(Y-H), capable of recognizing a CG mismatch site that is not recognized by natural nucleosides. After incorporating them into the oligonucleotides, their triplex forming abilities were evaluated by gel-shift assay. Although it was only one sequence, the 3′-GZG-5′ sequence, the stability of the CG mismatch site recognition was greatly improved compared with previous nucleoside analogues.

Original languageEnglish
Article number115782
JournalBioorganic and Medicinal Chemistry
Volume28
Issue number23
DOIs
Publication statusPublished - Dec 1 2020

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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