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[reaction: see text] A concise synthesis of a gramicidin S analogue with trisubstituted (E)-alkene dipeptide isostere (TEADI) replacements at both d-Phe-Pro positions was realized. Conformational analysis demonstrated that TEADIs can serve as type II beta-turn promoters in a cyclic scaffold and successfully mimic a proline residue.

Trisubstituted (E)-Alkene Dipeptide Isosteres as β-Turn Promoters in the Gramicidin S Cyclodecapeptide Scaffold