Fluorescence-tagged monolignols, p-hydroxycinnamyl alcohols ?-linked to fluorogenic dyes such as aminocoumarin, nitrobenzofuran, or styrylpyridinium derivatives, were synthesized and tested as photoprobes for in vitro and in vivo studies of cell wall lignification. The compatibility of the fluorescent monolignol derivatives in lignin polymerization was confirmed by in vitro peroxidase-catalyzed copolymerization of the compounds with monolignols yielding fluorescent dehydrogenation polymers. To illustrate the use of the compounds, we successfully monitored, in real time, the complexation of monolignols with horseradish apoperoxidase by F�rster resonance energy transfer (FRET), using the protein's tryptophan near the active site and an aminocoumarin moiety attached to monolignols as donor and acceptor fluorophores. In addition, to test an imaging approach, fluorescence-tagged monolignols were fed into developing plant cell walls from various plant species including Zea mays, Pinus radiata, and Arabidopsis thaliana; the resultant de novo fluorescent lignins could be readily visualized by fluorescence microscopy.

Fluorescence-tagged monolignols: New approaches to the study of cell wall lignification

243rd National Meeting (2012)

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