Regioselective prenylation of chalcones by a fungal prenyltransferase (AtaPT)

Abstract

Prenylation by prenyltransferases exhibits remarkable potential for chalcone modification owing to its high efficiency, specificity, and environmental benignity. The fungal-derived prenyltransferase AtaPT along with prenyl donors of different chain lengths was utilized in this study and five new prenylated chalcones (1G1, 1G2, 2G, 2D1, and 2D2) were chemoenzymatically synthesized. Notably, all prenyl groups were selectively incorporated into ring B of the chalcone scaffold, clearly demonstrating the exquisite regioselectivity of AtaPT. This work not only significantly expands the structural diversity of prenylated chalcones but also provides a biosynthetic module for the green and efficient preparation of prenylated chalcones in synthetic biology.