Multigram-Scale and Column Chromatography-Free Synthesis of L-Azetidine-2-carboxylic Acid for the Synthesis of Nicotianamine and Its Derivatives

Multigram-scale synthesis of L-azetidine-2-carboxylic acid from L-aspartic acid was achieved in 13 conventional synthetic steps, without the need for purification by silica-gel column chromatography and expensive reagents.Nicotianamine and its fluorescence-labeled derivatives could be obtained from this synthetic strategy.Nicotianamine (1), 1 which is biosynthesized from three molecules of (S)-adenosyl-L-methionine via nicotianamine synthase, is a metal-chelating molecule ubiquitous in higher plants. 2L-Azetidine-2-carboxylic acid (L-Aze 2) is a key chemical precursor to nicotianamine, deoxymugineic acid,