Progress toward the development of biomimetic organocatalysts for PET degradation

Abstract

Although conceptually simple, acyl substitution reactions such as transesterification and hydrolysis hold significant potential in diverse applications, including plastic degradation, biodiesel synthesis, and native chemical ligation. Various enzymes have been investigated as catalysts for acyl substitution reactions due to their high catalytic activity under mild conditions. However, their reliance on a stable 3D structure presents practical limitations. To address this, we aimed to develop small molecule organocatalysts that can mimic enzymatic activity while maintaining stability across various conditions. The catalyst is designed to mimic features of the protease active site, including an oxyanion hole that stabilizes the tetrahedral intermediate and an activated nucleophilic OH or SH group. We have applied this catalyst design for the glycolysis of PET (polyethylene terephthalate).