Stereochemistry as a Diversity Element: Solid-Phase Synthesis of Cyclic RGD Peptide Derivatives by Asymmetric Catalysis

Abstract

Dramatic differences in biological activity as a result of different conformations are exhibited by diastereomeric cyclic peptides such as 1 (only one diastereoisomer is shown) containing the universal cell-recognition sequence Arg-Gly-Asp, which were synthesized on amino alcohol templates. The amino alcohols were prepared by enantioselective ring opening of polymer-bound epoxides, a reaction that exemplifies the usefulness of enantioselective catalysis in combinatorial synthesis.