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ortho-Quinones and Analogues Thereof: Highly Reactive Intermediates for Fast and
Selective Biofunctionalization
#MMPMID29068513
Bruins JJ
; Albada B
; van Delft F
Chemistry
2018[Apr]; 24
(19
): 4749-4756
PMID29068513
show ga
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.