Toward mechanistic elucidation of iron acquisition in barley: efficient synthesis of mugineic acids and their transport activities.

摘要: Iron acquisition of graminaceous plants is characterized by the synthesis and secretion iron-chelating compounds, mugineic acids (MAs), a specific uptake system for MAs-iron(III) complexes. We identified transporter, HvYS1 (Hordeum vulgare L. yellow stripe 1), that highly in barley roots. In this article we outline characterization HvYS1, our recent work on practical syntheses MAs investigations into molecular basis transport their iron(III) complexes HvYS1. 2′-Deoxymugineic acid (DMA) was synthesized good overall yield from commercially available Boc-l-allylglycine using minimal number short simple operations with protecting groups work-up/purification procedures. The same strategy also successfully applied to β-hydroxy-l-allylglycine, which obtained an allylic oxidation l-allylglycine derivatives, give MA 2′-epi-MA efficiently. transported all three synthetic specimens efficiency similar natural complex. With sufficient quantities hand, analyzed function revealed preparing chimeric transporters sixth outer membrane loop transporter plays vital role substrate specificity. © 2010 Japan Chemical Journal Forum Wiley Periodicals, Inc. Chem Rec 10: 140–150; 2010: Published online InterScience (www.interscience.wiley.com) DOI 10.1002/tcr.200900028