Sulfonopeptides and Vinylogous-Sulfonamidopeptides

Sulfonamidopeptides can be considered as interesting candidates to find new protease inhibitors and new drugs, since the structure of the sulfonamide bond is similar to the tetrahedral transition state involved in the amide bond hydrolysis by proteolytic enzymes [33]. In the field of sulfonamide-containing peptidomimetics, several scaffolds have been proposed (Fig. 7.5). While the preparation of a-sulfonopeptides 5 has remained elusive [34,35], probably due to synthetic problems, such as p-elimination of S02, the other two types of oligomers turned out to be easily obtained. 

Synthetic P-sulfonopeptide-based receptors 9 and 10 were prepared using the diamino acid derivative 8 (Fig. 7.6) and screened for binding against an encoded library containing ca. 25 000 tripeptides [42]. 

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