CHED 865 |
| Brooke E Richardson, Department of Chemistry, Transylvania University, 300 N Broadway, Lexington, KY 40965 and Eva Csuhai, Division of Natural Science and Mathematics, Transylvania University, 300 North Broadway, Lexington, KY 40508. |
| Polyamines and their derivatives are potential targets for antitumor- or antiparasitic drugs. In our quest to synthesize new spermine analogs that will show enhanced binding to nardilysin, a highly negatively charged peptidase, we set out to add additional amino groups to spermine, a natural tetramine. In this work, a novel derivative of spermine that contains an additional aromatic amino group is synthesized. The added amino group is at one of the secondary nitrogens, in an attempt to create “enhanced” spermines for metal- and/or protein binding. The primary amino groups of spermine are protected by the addition of trifluoroacetyl groups. Trifluoroacetylated spermine is then added to trifluoroacetylated-4-bromomethylaniline to synthesize a secondary 4-aminobenzyl spermine. Finally, the trifluoroacetyl protecting groups are removed. The binding of the new derivative to metalloproteins like nardilysin will be tested by comparing its inhibitory behavior to spermine, a strong inhibitor of nardilysin, a zinc metallopeptidase. |
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Undergraduate Research Poster Session: Organic Chemistry
2:00 PM-4:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Chemical Education |