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Allylic amines as key building blocks in the synthesis of (E)-alkene peptide isosteres

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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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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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Skoda, EM
Davis, GC
Wipf, Ppwipf@pitt.eduPWIPF
Date: 20 January 2012
Date Type: Publication
Journal or Publication Title: Organic Process Research and Development
Volume: 16
Number: 1
Page Range: 26 - 34
DOI or Unique Handle: 10.1021/op2002613
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1083-6160
Article Type: Review
PubMed Central ID: PMC3272643
PubMed ID: 22323894
Date Deposited: 28 May 2013 15:12
Last Modified: 30 Oct 2017 23:57


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