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

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.

論文本文は2025-04-09以降公開予定
This is the peer reviewed version of the following article:Kimika Kayano, Tomohiro Tsutsumi, Yoshiko Murata, Chie Ogasa, Takehiro Watanabe, Ryota Sato, Sangita Karanjit, Kosuke Namba , Epoxide Ring-Opening Reactions for Abundant Production of Mugineic Acids and Nicotianamine Probes. Angewandte Chemie International Edition. 2024, 63, 20, e202401411, which has been published in final form at https://doi.org/10.1002/anie.202401411. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.