Controlling the Outcome of an N-Alkylation Reaction by Using N-Oxide Functional Groups

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Abstract

Covalent modifiers of proteins are of importance in chemical proteomics, an emerging chemical technology used to assign protein function. In this study, high-field H-1 NMR techniques were used to analyze the reaction of the bioactive compound, 2,3-bis(bromomethyl)quinoxaline 1,4-dioxide, with amines (a model system for proteins containing nitrogen-based nucleophiles). Unexpectedly, the results show that a double nucleophilic substitution reaction involving 2 equiv of the amine is preferred to an intramolecular cyclization pathway. A direct comparison with the reaction carried out on a substrate lacking the N-oxide functional groups is also provided. X-ray crystal structures and computational studies are used to rationalize the observed differences in reactivity between the two systems.

Original languageEnglish
Pages (from-to)5055-5061
Number of pages7
JournalThe Journal of Organic Chemistry
Volume70
Issue number13
DOIs
Publication statusPublished - 24 Jun 2005

Keywords

  • DERIVATIVES
  • ANALOGS
  • COMPLEX

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