Synthesis and spectroscopic characterization of binaphthol aminosugars for stimulation of DNA strand slippage synthesis

Liangliang Liu, Long Yi, Xing Yang, Zhihong Yu, Xin Wen, Zhen Xi

Research output: Contribution to journalArticle

Abstract

Expansion of DNA repeat sequences is associated with many human genetic diseases. Bulged DNA structures have been implicated as intermediates in DNA slippage within the DNA repeat regions. Two new binaphthol aminosugars were first synthesized as DNA bulge binders to study the triplet repeat expansion due to the wedge-shaped structure of 1,1′-bi-2-naphthol. Both compounds were structurally characterized by 1- and 2-D NMR. They showed remarkable fluorescence enhancement when binding with bulge DNA and they exhibited stimulation for ATT·AAT trinucleotide repeat DNA sequence slippage synthesis.

Original languageEnglish (US)
Pages (from-to)5885-5890
Number of pages6
JournalTetrahedron
Volume64
Issue number25
DOIs
StatePublished - Jun 16 2008

Keywords

  • Binaphthol
  • DNA
  • Slippage synthesis
  • Trinucleotide repeat
  • Wedge-shaped structure

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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