Rational design, synthesis and biological evaluation of the first inhibitor of lignin polymerization

A fluorinated analogue of coniferin (the glucoside of coniferyl alcohol) has been synthesized in three steps from vanillin tetraacetyl glucoside; bearing a fluorine atom on the beta position of the propenyl side chain which is involved in the main site of coupling, it is designed as a potential inhibitor of oxidases involved in the biosynthesis of lignin, and in vivo experiments show a pronounced inhibition of lignin biosynthesis in poplar plantlets, with a five-fold decrease in lignin formed.