Skoda, EM and Davis, GC and Wipf, P
(2012)
Allylic amines as key building blocks in the synthesis of (E)-alkene peptide isosteres.
Organic Process Research and Development, 16 (1).
26 - 34.
ISSN 1083-6160
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Abstract
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. © 2012 American Chemical Society.
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