Highly efficient synthesis of DNA-binding hairpin polyamides via the use of a new triphosgene coupling strategy

Wu Su, Stephen J Gray, Ruggero Dondi, Glenn Burley

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

A facile and highly efficient solid phase synthesis method is reported for the preparation of hairpin DNA-binding polyamides using the cost-effective
triphosgene (BTC) activating agent. Difficult polyamide sequences were prepared from N-methylimidazole (Im) and N-methylpyrrole (Py) building blocks with high stepwise yields (>98%) using Boc chemistry. The versatility of the triphosgene coupling approach was also demonstrated for the first time on aryl hydrazine resins to afford biomedically relevant tail-truncated polyamides in excellent isolated yields.
Original languageEnglish
Pages (from-to)3910-3913
Number of pages4
JournalOrganic Letters
Volume11
Issue number17
Early online date11 Aug 2009
DOIs
Publication statusPublished - 3 Sep 2009

Keywords

  • solid phase synthesis
  • hairpin DNA-binding polyamides
  • polyamide sequences

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