A Practical Synthesis of the Phytosiderophore 2′-Deoxymugineic Acid: A Key to the Mechanistic Study of Iron Acquisition by Graminaceous Plants

2007 ◽  
Vol 119 (37) ◽  
pp. 7190-7193 ◽  
Author(s):  
Kosuke Namba ◽  
Yoshiko Murata ◽  
Manabu Horikawa ◽  
Takashi Iwashita ◽  
Shoichi Kusumoto
Keyword(s):  
Iron Acquisition ◽  
Mechanistic Study ◽  
Deoxymugineic Acid ◽  
Practical Synthesis ◽  
Graminaceous Plants

Comparison of iron acquisition from Fe–pyoverdine by strategy I and strategy II plants

Botany ◽  
2011 ◽  
Vol 89 (10) ◽  
pp. 731-735 ◽  
Author(s):  
Matt Shirley ◽  
Laure Avoscan ◽  
Eric Bernaud ◽  
Gérard Vansuyt ◽  
Philippe Lemanceau
Keyword(s):  
Arabidopsis Thaliana ◽  
Plant Species ◽  
Iron Uptake ◽  
Iron Acquisition ◽  
Iron Status ◽  
Iron Nutrition ◽  
Perennial Species ◽  
Major Class ◽  
Graminaceous Plants ◽  
Strategy I

Iron is an essential micronutrient for plants and associated microorganisms. However, the bioavailability of iron in cultivated soils is low. Plants and microorganisms have thus evolved active strategies of iron uptake. Two different iron uptake strategies have been described in dicotyledonous and monocotyledonous graminaceous species. In bacteria, this strategy relies on the synthesis of siderophores. Pyoverdines, a major class of siderophores produced by fluorescent pseudomonads, were previously shown to promote iron nutrition of the dicotyledonous species Arabidopsis thaliana L. (Heynh.), whereas contradictory reports were made on the contribution of those siderophores to the nutrition of graminaceous annuals. Furthermore, no information has so far been available on graminaceous perennials. Here, the contribution of purified pyoverdine of Pseudomonas fluorescens C7R12 to the iron nutrition of two annual and perennial graminaceous plants was assessed and compared with that of two dicotyledonous plant species. Fe–Pyoverdine promoted the iron status of all plant species tested. With the exception of wheat, this promotion was more dramatic in graminaceous species than in dicotyledonous species and was the highest in fescue, a perennial species. The incorporation of 15N-labeled pyoverdine was consistent with the effect on the iron status of the plants tested.

A short practical synthesis of 2′-deoxymugineic acid

2005 ◽  
Vol 46 (9) ◽  
pp. 1419-1421 ◽  
Author(s):  
Satendra Singh ◽  
George Crossley ◽  
Saswati Ghosal ◽  
Yann Lefievre ◽  
Michael W. Pennington
Keyword(s):  
Deoxymugineic Acid ◽  
Practical Synthesis

scholarly journals Base-catalyzed C-alkylation of potassium enolates with styrenes via a metal–ene reaction: a mechanistic study

2020 ◽  
Vol 18 (11) ◽  
pp. 2063-2075 ◽  
Author(s):  
Joshua P. Barham ◽  
Thierry N. J. Fouquet ◽  
Yasuo Norikane
Keyword(s):  
Kinetic Studies ◽  
Mechanistic Study ◽  
Ene Reaction ◽  
Practical Synthesis

Base-catalyzed, C-Alkylation of potassium (K) Enolates with Syrenes (CAKES) enables practical synthesis or elaboration of pharmaceutical cores via a thusfar elusive mechanism. Herein, computational (DFT) and kinetic studies back a metal-ene reaction.

scholarly journals Development of a mugineic acid family phytosiderophore analog as an iron fertilizer

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Motofumi Suzuki ◽  
Atsumi Urabe ◽  
Sayaka Sasaki ◽  
Ryo Tsugawa ◽  
Satoshi Nishio ◽  
...  
Keyword(s):  
Calcareous Soil ◽  
Alkaline Soils ◽  
Soil Application ◽  
Deoxymugineic Acid ◽  
Essential Nutrient ◽  
Agricultural Use ◽  
Practical Synthesis ◽  
Low Solubility ◽  
Poor Stability ◽  
Iron Fertilizer

AbstractIron (Fe) is an essential nutrient, but is poorly bioavailable because of its low solubility in alkaline soils; this leads to reduced agricultural productivity. To overcome this problem, we first showed that the soil application of synthetic 2′-deoxymugineic acid, a natural phytosiderophore from the Poaceae, can recover Fe deficiency in rice grown in calcareous soil. However, the high cost and poor stability of synthetic 2′-deoxymugineic acid preclude its agricultural use. In this work, we develop a more stable and less expensive analog, proline-2′-deoxymugineic acid, and demonstrate its practical synthesis and transport of its Fe-chelated form across the plasma membrane by Fe(III)•2’-deoxymugineic acid transporters. Possibility of its use as an iron fertilizer on alkaline soils is supported by promotion of rice growth in a calcareous soil by soil application of metal free proline-2’-deoxymugineic acid.

ChemInform Abstract: Practical Synthesis and Mechanistic Study of Polysubstituted Tetrahydropyrimidines with Use of Domino Multicomponent Reactions.

ChemInform ◽  
2009 ◽  
Vol 40 (39) ◽  
Author(s):  
Qiuhua Zhu ◽  
Huanfeng Jiang ◽  
Jinghao Li ◽  
Min Zhang ◽  
Xiujun Wang ◽  
...  
Keyword(s):  
Multicomponent Reactions ◽  
Mechanistic Study ◽  
Practical Synthesis

Practical synthesis and mechanistic study of polysubstituted tetrahydropyrimidines with use of domino multicomponent reactions

Tetrahedron ◽  
2009 ◽  
Vol 65 (23) ◽  
pp. 4604-4613 ◽  
Author(s):  
Qiuhua Zhu ◽  
Huanfeng Jiang ◽  
Jinghao Li ◽  
Min Zhang ◽  
Xiujun Wang ◽  
...  
Keyword(s):  
Multicomponent Reactions ◽  
Mechanistic Study ◽  
Practical Synthesis

scholarly journals Cloning and Characterization of Deoxymugineic Acid Synthase Genes from Graminaceous Plants

2006 ◽  
Vol 281 (43) ◽  
pp. 32395-32402 ◽  
Author(s):  
Khurram Bashir ◽  
Haruhiko Inoue ◽  
Seiji Nagasaka ◽  
Michiko Takahashi ◽  
Hiromi Nakanishi ◽  
...  
Keyword(s):  
Amino Acids ◽  
Vascular Bundles ◽  
Long Distance ◽  
Mugineic Acid Family Phytosiderophores ◽  
Long Distance Transport ◽  
Shoot Tissue ◽  
Iron Deficient ◽  
Deoxymugineic Acid ◽  
Graminaceous Plants

Graminaceous plants have evolved a unique mechanism to acquire iron through the secretion of a family of small molecules, called mugineic acid family phytosiderophores (MAs). All MAs are synthesized from l-Met, sharing the same pathway from l-Met to 2′-deoxymugineic acid (DMA). DMA is synthesized through the reduction of a 3″-keto intermediate by deoxymugineic acid synthase (DMAS). We have isolated DMAS genes from rice (OsDMAS1), barley (HvDMAS1), wheat (TaD-MAS1), and maize (ZmDMAS1). Their nucleotide sequences indicate that OsDMAS1 encodes a predicted polypeptide of 318 amino acids, whereas the other three orthologs all encode predicted polypeptides of 314 amino acids and are highly homologous (82–97.5%) to each other. The DMAS proteins belong to the aldo-keto reductase superfamily 4 (AKR4) but do not fall within the existing subfamilies of AKR4 and appear to constitute a new subfamily within the AKR4 group. All of the proteins showed DMA synthesis activity in vitro. Their enzymatic activities were highest at pH 8–9, consistent with the hypothesis that DMA is synthesized in subcellular vesicles. Northern blot analysis revealed that the expression of each of the above DMAS genes is up-regulated under iron-deficient conditions in root tissue, and that of the genes OsDMAS1 and TaDMAS1 is up-regulated in shoot tissue. OsDMAS1 promoter-GUS analysis in iron-sufficient roots showed that its expression is restricted to cells participating in long distance transport and that it is highly up-regulated in the entire root under iron-deficient conditions. In shoot tissue, OsDMAS1 promoter drove expression in vascular bundles specifically under iron-deficient conditions.

scholarly journals Cloning Two Genes for Nicotianamine Aminotransferase, a Critical Enzyme in Iron Acquisition (Strategy II) in Graminaceous Plants

1999 ◽  
Vol 121 (3) ◽  
pp. 947-956 ◽  
Author(s):  
Michiko Takahashi ◽  
Hirotaka Yamaguchi ◽  
Hiromi Nakanishi ◽  
Takayuki Shioiri ◽  
Naoko-Kishi Nishizawa ◽  
...  
Keyword(s):  
Iron Acquisition ◽  
Acquisition Strategy ◽  
Graminaceous Plants
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