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. Author manuscript; available in PMC: 2017 Oct 1.
Published in final edited form as: Curr Opin Chem Biol. 2016 Sep 10;34:110–116. doi: 10.1016/j.cbpa.2016.08.011

Figure 4.

Figure 4

Reversible covalent chemistry of amines. a) PLP-elicited imine formation. b) Coumarin 3-aldehyde based sensors for the detection of important amine-presenting metabolites. The table presents the substrate specificity of several sensors. c) A boronic acid-derivatized coumarin 3-aldehyde probe selectively binds glucosamine through cooperative imine and boronate ester formation. d) A molecular probe for the detection of histone deacetylase activity in live cells. e) Reversible iminoboronate formation of biological amines. f) Cartoon illustration of lysine side modification of proteins through iminoboronate formation. g) Illustration of bacterial labeling through iminoboronate formation of bacterial lipids. Shown on the right is a confocal image showing membrane labeling of S. aureus cells via iminoboronate chemistry.