ORGN 442 |
Synthesis of azapeptide analogues of Freidinger dipeptide lactams
| Robert L. Broadrup and William P. Malachowski. Department of Chemistry, Bryn Mawr College, 101 North Merion Ave., Bryn Mawr, PA 19010 |
| Peptidomimetic structures are important for their ability to mimic the biological activity of their natural counterparts, while exhibiting greater metabolic stability. The seminal work of Freidinger with dipeptide lactams is a classic example of peptidomimetic structures that have been frequently used for this purpose. Azapeptide analogues of Freidinger lactams have now been synthesized via intramolecular Mitsunobu reaction of azapeptide-serine or azapeptide-serine homologues. Serine homologues have been synthesized from aspartic and glutamic acid derivatives. The serine homologues were coupled with azapeptides and cyclized under Mitsunobu conditions. These methods provide a concise, unified manner to generate dipeptide lactams with a range of ring sizes. 
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Total Synthesis, Process R&D, Combinatorial, Bioorganic, Physical Organic Chemistry
8:00 PM-10:00 PM, Tuesday, August 24, 2004 Pennsylvania Convention Center -- Hall D, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- Hall D, Sci-Mix
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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