Affiliation:
1. Department of Cancer Biology, Dana-Farber Cancer Institute
2. Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School
Abstract
AbstractEnamine N-oxides act as a chemical linchpin bridging two bioorthogonal associative and dissociative reactions. This article describes the design of enamine N-oxides, their synthesis through the retro-Cope elimination reaction, the use of solvent, hyperconjugation, strain, and rehybridization effects to achieve bioorthogonal reactivity, and their rapid reductive cleavage with diboron reagents. The coordinated assembly and disassembly of the enamine N-oxide motif constitutes a powerful chemical operation that enables the attachment and detachment of small molecules from biomacromolecules in a biological setting.1 Introduction2 Background3 General Access to Linear Enamine N-Oxides4 Strain-Promoted Hydroamination Reaction5 Electronically Activated Alkynes6 Chemically Revertible Reactions7 Conclusion
Funder
Claudia Adams Barr Program for Innovative Cancer Research
National Institute of Environmental Health Sciences