EPR imaging of sinapyl alcohol and its application to the study of plant cell wall lignification

Abstract

Bioorthogonal chemical reporter strategy can be successfully combined with EPR spectroscopy in plant tissues to detect the incorporation of a tagged monolignol into the lignin polymer.

Live‐Cell Imaging of Sterculic Acid—a Naturally Occurring 1,2‐Cyclopropene Fatty Acid—by Bioorthogonal Reaction with Turn‐On Tetrazine‐Fluorophore Conjugates**

“…Surprisingly the H‐tetrazine 8 showed little turn‐on in PBS. It has previously been suggested that H‐tetrazines can be too unstable to be used in biological applications, [55] and upon stability assessment of our tetrazine library in PBS (Figure S3A) it is clear that 8 is somewhat prone to degradation over time. Thereby the reaction between 1 and 8 cannot go to completion because of competition with hydrolytic degradation and unquenching of the H‐tetrazine.…”

Synthesis of novel lignin model compounds labeled with alkynyl and their potential application

“…8–10 Biorthogonal methods were recently applied to elucidate the lignification kinetics of plant cell walls since lignin cannot be observed in vivo through gene labeling like proteins. 11–13…”

“…[8][9][10] Biorthogonal methods were recently applied to elucidate the lignification kinetics of plant cell walls since lignin cannot be observed in vivo through gene labeling like proteins. [11][12][13] In 2011, Tobimatsu and his coworkers designed and synthesized two new fluorescent labeled lignin precursor monomers, CADMAC (dimethylaminocoumarin tagged coniferyl alcohol) and CANBD (nitrobenzofuran tagged coniferyl alcohol). 14 Copolymerization was carried out in vitro with horseradish peroxidase, and the complexation was monitored in real time.…”