Synthesis of [13C4]-labeled 2'-deoxymugineic acid.
The phytosiderophore 2'-deoxymugineic acid (DMA) is exuded via the root system by all grasses (including important crop plants like rice, wheat and barley) to mobilize Fe(III) from soil and improve plant Fe nutrition, crucial for high crop yields. Elucidation of the biogeochemistry of 2'-deoxymugineic acid in the rhizosphere requires its quantification in minute amounts. To this end, (13)C4-DMA was synthesized for the first time, from cheap isotopically labeled starting materials. The synthetic route utilizes L-allyl((13)C2)glycine and L-(2-(13)C)azetidine ((13)C)carboxylic acid as versatile labeled building blocks. The title compound was recently used as an internal standard for analysis of soil and plant samples allowing the first accurate quantification of DMA in these matrices by means of LC-MS/MS. It is furthermore used in tracer experiments investigating biodegradation of DMA in soil.
Department of Chemistry, University of Natural Resources and Life Sciences-Vienna, Muthgasse 18, A-1190, Vienna, Austria.
Martin R
MR
Walter
Daniel
D
Artner
Christian
C
Stanetty
D001383:Azetidinecarboxylic Acid / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry; D002247:Carbon Isotopes / Q000737:chemistry; D007553:Isotope Labeling; D012987:Soil / Q000737:chemistry
D002247:Carbon Isotopes; D012987:Soil; D001383:Azetidinecarboxylic Acid; C052864:2'-deoxymugineic acid; C052863:mugineic acid
13C-isotopically labeled compound; 2′-deoxymugineic acid; internal LC-MS/MS standard; phytosiderophore; soil chemistry