Synthesis of p-amino-WNA derivatives to enhance the stability of the anti-parallel triplex

Yosuke Taniguchi, Mieko Togo, Eriko Aoki, Yuko Uchida, Shigeki Sasaki

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

We have previously developed W-shaped nucleoside analogs (WNAs) having a nucleobase and an aromatic ring for the formation of the unnatural triplex DNA. Modification of an aromatic ring of WNA is highly effective regarding the stability of the triplex DNA. In this study, we designed new WNA analogs having the p-aminobenzene as an aromatic ring, which were synthesized via the Curtius-Yamada rearrangement. Based on the evaluation of the triplex formation with p-amino-WNA-TFO, it has been shown that the amino group may produce a non-selective interaction with the phosphate backbone of the target duplexes. These results indicate that the amino modification is useful to overcome the sequence-dependence of the TFO containing WNA analogs.

Original languageEnglish
Pages (from-to)7164-7170
Number of pages7
JournalTetrahedron
Volume64
Issue number30-31
DOIs
Publication statusPublished - Jul 21 2008

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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