ortho‐Quinones and Analogues Thereof: Highly Reactive Intermediates for Fast and Selective Biofunctionalization

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. Combine...

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Veröffentlicht in:Chemistry : a European journal 2018-04, Vol.24 (19), p.4749-4756
Hauptverfasser: Bruins, Jorick J., Albada, Bauke, van Delft, Floris
Format: Artikel
Sprache:eng
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Zusammenfassung: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. Ortho‐quinones, generated in situ by oxidation of catechols or phenols, readily undergo Michael addition or Diels–Alder cycloaddition, thereby enabling fast and selective protein functionalization.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201703919