Ortho-Quinones and Analogues Thereof: Highly Reactive Intermediates for Fast and Selective Biofunctionalization

Jorick J. Bruins, Bauke Albada, Floris van Delft*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

21 Citations (Scopus)

Abstract

Fast, selective and facile functionalization of biologically relevant molecules is a pursuit of ever-growing importance. A promising approach in this regard employs the high reactivity of quinone and quinone analogues for fast conjugation chemistry by nucleophilic addition or cycloadditions. Combined with in situ generation of these compounds, selective conjugation on proteins and surfaces can be uniquely induced in a time and spatially resolved manner: generation of a quinone can often be achieved by simple addition of an enzyme or stoichiometric amounts of chemoselective oxidant, or by exposure to light. In this Minireview, we discuss the generation and subsequent functionalization of quinones, iminoquinones, and quinone methides. We also discuss practical applications regarding these conjugation strategies.
Original languageEnglish
Pages (from-to)4749-4756
JournalChemistry - A European Journal
Volume24
Issue number19
Early online date19 Dec 2017
DOIs
Publication statusPublished - 3 Apr 2018

Keywords

  • Addition reactions
  • Biochemistry
  • Heterocycles
  • Nucleophiles
  • Quinones

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