2,-Deoxymugineic acid

S. Shojima, N. Nishizawa, S. Fushiya, S. Nozoe, T. Irifune, and S. Mori, Biosynthesis of phytosiderophores in vitro biosynthesis of 2 -deoxymugineic acid from L-methionine and nicotianamine. Plant Phy.siol. 93 1491 (1990). 

Ohfune, Y., Tomita, M., and Nomoto, K. (1981). Total synthesis of 2 -deoxymugineic acid, the metal chelator excreted from wheat root. J. Am. Chem. Soc. 103, 2409-2410. 

THP-Protected butyrolactone 289 is one of the chiral fragments used in the total synthesis of 2 -deoxymugineic acid (295), a metal chelator excreted from wheat root (Scheme 40) [91]. The sequence 275 —> 291 proceeds with an overall yield of 55%. 

Deoxymugineic acid (295), a third constituent of Avena sativa, is prepar H K animation of 348 with amine diester 358 (58% yield). Compound 358 is in turn reductive amination of 353 with L-azetidine-2-carboxylic acid. prepared by... 

Fig. 3. Distribution of metal-2 -deoxymugineic acid (DMA) in solution as a function of pH. Metal binding by the soil solid phase is simultaneously considered using empirically derived solubilities. For Cd, Zn, Cu, and Ni the empirical solubility model used was log (M"+) = a + b pH + c log Mj + d log OM, where a is an empirical constant (intercept) and the other three coefficients reflect the dependence of solubility on pH, total soil metal content and organic matter (or carbon), respectively. Fe(OH)j had an assumed solubility of log K = —2.1 (Lindsay, 1979). The total soil metal concentration was 10 mg kg , organic C was 10 g kg and DMA was 25 iM.

Nomoto, K., Yoshioka, H., Arima, M., Fushiya, S., Takagi, S., Takemoto, T., 1981. Structure of 2 -deoxymugineic acid, a novel amino-acid possessing an iron-chelating activity. Chimia 35, 249-250. 

Reichman, S.M., Parker., D.R., 2002. Revisiting the metal-binding chemistry of nicotianamine and 2 -deoxymugineic acid. Implications for iron nutrition in Strategy II plants. Plant Physiol. 129, 1435-1438. 

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