Solid-phase synthesis of homodetic cyclic peptides from Fmoc-MeDbz-resin. Issue 18 (2nd May 2018)

• Record Type: Journal Article
• Authors: Abdel Monaim, Shimaa A.H.; Acosta, Gerardo A.; Royo, Miriam; El-Faham, Ayman; de la Torre, Beatriz G.; Albericio, Fernando
• Is Part Of: Tetrahedron letters. Volume 59:Issue 18(2018)
• Page Start: 1779
• Page End: 1782
• Publication Date: 2018-05-02
• Subjects: Cyclic peptides -- Cyclactive cleavage -- MeDbz linker -- Solid-phase peptide synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.03.084
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Efficient solid-phase synthesis of homodetic cyclic peptides. MeDbz linker as a safety catch linker. High purity of final cyclic peptides thanks to the cyclative cleavage. Abstract: Cyclic homodetic peptides are very appealing for medicinal chemistry programs. In addition to the high efficiency and selectivity inherently associated with peptides, a cyclic structure totally formed by amide bonds increases their stability under physiological conditions. Here Fmoc-MeDbz-resin was studied for the preparation of these peptides. Our results demonstrate the usefulness of this strategy for the preparation of cyclic "head-to-side chain" peptides through cyclative cleavage (simultaneous cyclization and release from the resin). In contrast, for the synthesis of the "head-to-tail" counterparts, the cyclization-cleavage should be carried out in the presence of thiophenol.