A cyclopentane conformational restraint for a peptide nucleic acid: Design, asymmetric synthesis, and improved binding affinity to DNA and RNA

Michael C. Myers, Mark A. Witschi, Nataliya V. Larionova, John M. Franck, Russell D. Haynes, Toshiaki Hara, Andrzej Grajkowski, Daniel H. Appella

Research output: Contribution to journalArticle

44 Scopus citations

Abstract

(Matrix presented) A strategy to restrict the highly flexible backbone conformation of a peptide nucleic acid (PNA) by incorporation of a cyclopentane ring is proposed. An asymmetric synthesis of cyclopentane-modified PNA is reported, and its binding properties were determined. The cyclopentane ring leads to a significant improvement in the binding properties of the resulting PNA to DNA and RNA.

Original languageEnglish (US)
Pages (from-to)2695-2698
Number of pages4
JournalOrganic Letters
Volume5
Issue number15
DOIs
StatePublished - Jul 24 2003
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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