TY  - JOUR
ID  - pittir18732
UR  - http://d-scholarship-dev.library.pitt.edu/18732/
IS  - 1
A1  - Skoda, EM
A1  - Davis, GC
A1  - Wipf, P
Y1  - 2012/01/20/
N2  - 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 ?-turn secondary structures and display impressive biological properties including selective reactions with reactive oxygen species (ROS) and prevention of apoptosis. © 2012 American Chemical Society.
JF  - Organic Process Research and Development
VL  - 16
SN  - 1083-6160
TI  - Allylic amines as key building blocks in the synthesis of (E)-alkene peptide isosteres
SP  - 26 
AV  - public
EP  -  34
ER  -