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

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 compo...

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Bibliographic Details
Published in:Journal of chemical education 1996-11, Vol.73 (11), p.1036
Main Authors: Mosher, Michael D, Verner, Erik J, Oliver, Bradford J, Hamlin, Daniel, Vietri, Nicholas, Palmer, Robert B, Arnold, Tyrone V, Natale, Nicholas R
Format: Article
Language:English
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Summary: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.
ISSN:0021-9584
1938-1328
DOI:10.1021/ed073p1036