Synthesis of N-Methyl-2-trichloroacetylpyrrole-A Key Building Block in Peptides That Bind DNA: Micro-, Semimicro-, and Macro-Scale Organic Lab Experiments

• Michael D. Mosher ^[1] ; Erik J. Verner ^[1] ; Bradford J. Oliver ^[1] ; Daniel Hamlin ^[1] ; Nicholas Vietri ^[1] ; Robert B. Palmer ^[1] ; Tyrone V. Arnold ^[1] ; Nicholas R. Natale ^[1]
  1. [1] University of Idaho

     University of Idaho

     Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 73, Nº 11 (November), 1996, págs. 1036-1039
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • The search for more efficient anticancer and antiviral agents has included the preparation and testing of a wide variety of molecules that bind DNA. Of these, particular attention has been devoted to the synthesis of analogues of DNA minor-groove binders such as netropsin and distamycin. These compounds have been shown to exhibit biological activity through their strong interactions with the DNA minor groove, and a relationship between their structure and biological activity has emerged (1). The repeating pyrrole unit contained in these compounds can be prepared from N-methylpyrrole via a noncatalyzed Friedel-Crafts acylation. The reaction has been adapted for use in the undergraduate organic chemistry laboratory on three different scales: microscale, semimicroscale, and macroscale.