Details

Autor(en) / Beteiligte

• Skoda, Erin M
• Davis, Gary C
• Wipf, Peter

Titel

Allylic Amines as Key Building Blocks in the Synthesis of (E)-Alkene Peptide Isosteres

Ist Teil von

• Organic process research & development, 2012-01, Vol.16 (1), p.26-34

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2012

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Nucleophilic imine additions with vinyl organometallics have developed into efficient, high-yielding, and robust methodologies to generate structurally diverse allylic amines. We have used the hydrozirconation/transmetalation/imine addition protocol in the synthesis of allylic amine intermediates for peptide bond isosteres, phosphatase inhibitors, and mitochondria-targeted peptide mimetics. The gramicidin S-derived XJB-5-131 and JP4-039 and their analogues have been prepared on up to 160-g scale for preclinical studies. These (E)-alkene peptide isosteres adopt type II′ β-turn secondary structures and display impressive biological properties including selective reactions with reactive oxygen species (ROS) and prevention of apoptosis.