Prev. Article Next Article Table of Contents

Article

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

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

PDF/HTML,
figures/images,
references and tables,
(where available)

Michael D. Mosher , Erik J. Verner , Bradford J. Oliver , Daniel Hamlin , Nicholas Vietri , Robert B. Palmer , Tyrone V. Arnold and Nicholas R. Natale

301 Renfrew Hall, Department of Chemistry, University of Idaho, Moscow, ID 83844-2343

J. Chem. Educ., 1996, 73 (11), p 1036

DOI: 10.1021/ed073p1036

Publication Date (Web): November 1, 1996

Section:

History, Education, and Documentation

Abstract

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.