ORGN 792 |
| Xuyuan Gu, Jinfa Ying, Jimes P. Cain, Byoung Min, and Victor J. Hruby. Hruby group, Department of Chemistry, University of Arizona, 1306 E. University, Tucson, AZ 85721 |
| Bicyclic dipeptide reverse turns occupy a very important position in peptidomimetic research. It is tremendously important to develop such a methodology so that different sizes of bicyclic dipeptide can be inserted into targeted peptides by combinatorial chemistry. Here we report a novel strategy which generates all possible sizes of bicyclic scaffolds inserted into peptides using Fmoc based nonconventional solid-phase synthesis. This methodology is well illustrated by the synthesis of [3.3.0]-, [4.3.0.]-, and [5.3.0]- bicyclic Leu-enkephalin analogues on Wang resin. The chemistry was carefully optimized and the configurations were confirmed by 2D NMR. The SAR and MCMM modeling studies will be discussed. [Supported by grants from the USPHS and NIDA.] |
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Combinatorial, Parallel, and Solid-Phase Chemistry
1:00 PM-5:00 PM, Thursday, August 26, 2004 Pennsylvania Convention Center -- 202B, Oral
Division of Organic Chemistry |