期刊
ORGANIC PROCESS RESEARCH & DEVELOPMENT
卷 16, 期 1, 页码 26-34出版社
AMER CHEMICAL SOC
DOI: 10.1021/op2002613
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资金
- NSF
- NIH
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0910560] Funding Source: National Science Foundation
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' beta-turn secondary structures and display impressive biological properties including selective reactions with reactive oxygen species (ROS) and prevention of apoptosis.
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