Epoxide Ring‐Opening Reactions for Abundant Production of Mugineic Acids and Nicotianamine Probes

Abstract

A succinct synthetic approach to mugineic acids and 2’‐hydroxynicotianamine was established. Unlike all other synthetic methods, this approach utilized epoxide ring‐opening reactions to form two C‐N bonds and is characterized by the absence of redox reactions. Mugineic acid was synthesized from three readily available fragments on a gram scale in 6 steps. The protected 2’‐hydroxynicotianamine was also synthesized in 4 steps, and the dansyl group, serving as a fluorophore, was introduced through a click reaction after propargylation of the 2’‐hydroxy group. The dansyl‐labeled nicotianamine (NA) iron complexes were internalized by oocytes overexpressing ZmYS1 (from maize) or PAT1 (from human) transporters, indicating successful transport of the synthesized NA‐probe through these transporters.