Total synthesis of [13C2] ‐labeled phytosiderophores of the mugineic and avenic acid families

In this work, we report the modular synthesis of all naturally occurring members from the mugineic acid and avenic acid family in13C2-labeled form. The syntheses commence from available13C2-bromoacetic acid and13C2-glycine delivering labeled building blocks13C2-l-allylglycine and a related hydroxylated derivative, both potentially valuable for other synthetic routes toward labeled (natural) products. We, herein, report the synthesis of13C2-labeled natural products from the mugineic acid and avenic acid family. These phytosiderophores ( “plant iron carriers”) are built up from non-proteinogenic amino acids and play a key role in micronutrient uptake in gramineous plants. In this work, two central building blocks are prepared from labeled starting materials (13C2-bromoacetic acid,13C2-glycine) and further employed in our recently reported divergent, branched synthetic strategy delivering eight isotopically labeled phytosiderophores. The required labeled building blocks (13C2-l-allylglycine and a related hydroxylated derivative) were prepared via enantioselective phase-transfer catalysis and enantio- and diastereoselective aldol condensation with a chiral auxiliary, respectively, both potentially valuable themselves for other synthetic routes toward labeled (natural) products.

Source: Journal of Labelled Compounds and Radiopharmaceuticals - October 2, 2023 Category: Biochemistry Authors: Nicolas Kratena, Markus Draskovits, Nina Biedermann, Eva Oburger, Christian Stanetty Tags: RESEARCH ARTICLE Source Type: research