Synthesis of phosphonocinnamic thioesters, substrate analogues of cinnamoyl-CoA reductase, a key enzyme in the lignification process

Caroline Lapeyre (1) , Florence Bedos-Belval (1) , Hubert Duran (1) , Michel Baltas (1) , Liliane Gorrichon (1)

1 SPCMIB - Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique

The one-pot transesterification of diethylarylvinylphosphonates with N-acetylcysteamine has been achieved using phosphonochloridates as intermediates. Reaction of phosphonodiesters with (COCl)2 gave the corresponding chlorinated compounds, which were coupled with N-acetylcysteamine in presence of Et3N.

Mots clés: lignification; thioesters; phosphonothioesters; cinnamoyl-CoA reductase

Domaines: Chimie

Caroline Lapeyre, Florence Bedos-Belval, Hubert Duran, Michel Baltas, Liliane Gorrichon. Synthesis of phosphonocinnamic thioesters, substrate analogues of cinnamoyl-CoA reductase, a key enzyme in the lignification process. Tetrahedron Letters, 2003, 44 (12), pp.2445-2447. ⟨10.1016/S0040-4039(03)00349-6⟩. ⟨hal-02444187⟩