Coumarin base-pair replacement as a fluorescent probe of ultrafast DNA dynamics

Robert S. Coleman, Mark A. Berg, Catherine J. Murphy

Research output: Contribution to journalArticlepeer-review

Abstract

The design and synthesis of a novel coumarin C-riboside are described, and is based on the well-known photoprobe Coumarin 102. A diastereofacial selective Heck coupling between a furanoid glycal and a coumarin triflate provided a method for glycoside formation. The coumarin C-glycoside was incorporated synthetically into DNA oligomers, and was used to probe ultrafast dynamics of duplex DNA using time-resolved Stokes shift methods.

Original languageEnglish (US)
Pages (from-to)3450-3456
Number of pages7
JournalTetrahedron
Volume63
Issue number17
DOIs
StatePublished - Apr 23 2007
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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