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1996
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In the Laboratory
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Synthesis of N-Methyl-2-trichloroacetylpyrrole-A Key Building Block in Peptides That Bind DNA: Micro-, Semimicro-, and Macro-Scale Organic Lab Experiments
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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
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November 1996
Vol. 73 No. 11
p. 1036
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| Abstract |
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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.
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| More Information |
 Citation |
Mosher, Michael D.; Verner, Erik J.; Oliver, Bradford J.; Hamlin, Daniel; Vietri, Nicholas; Palmer, Robert B.; Arnold, Tyrone V.; Natale, Nicholas R. J. Chem. Educ. 1996 73 1036.
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Keywords |
Biochemistry
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History |
Created:
Last Updated: |
August 5, 1999
February 21, 2006
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| Home > JCE Print > Journal of Chemical Education > Issues >
1996
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November
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1036
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