A short practical synthesis of 2′-deoxymugineic acid

Singh, Satendra; Crossley, George H.; Ghosal, Saswati; Lefievre, Yann; Pennington, Michael W.

doi:10.1016/j.tetlet.2005.01.030

Cited by 34 publications

(7 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…DMA is costly to synthesize because it requires large amounts of expensive l -azetidine-2-carboxylic acid as the starting material 24 , 30 – 34 , and the instability of DMA is likely caused by the highly strained four-membered ring of azetidine-2-carboxylic acid. To address these critical issues, we investigated the synthesis and use of alternatives to l -azetidine-2-carboxylic acid, by transitioning from a four-membered azetidine ring to a five-membered ring with the aim of reducing molecular strain and improving the resistance to biodegradation.…”

Section: Resultsmentioning

confidence: 99%

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

Suzuki¹,

Urabe

Sasaki

et al. 2021

Nat Commun

View full text Add to dashboard Cite

Iron (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.

show abstract

Section: Resultsmentioning

confidence: 99%

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

Suzuki¹,

Urabe

Sasaki

et al. 2021

Nat Commun

View full text Add to dashboard Cite

show abstract

“…This complexation strategy renders grass species more efficient in Fe acquisition compared to non‐grass species, particularly in high pH soil, where soluble Fe concentrations are low. Investigations into plants molecular mechanisms, and consequently efforts towards the synthesis of these natural products have been reported since the late 1970s [5a–h] …”

Section: Figurementioning

confidence: 99%

A Unified Approach to Phytosiderophore Natural Products

Kratena

Gökler

Oburger³

et al. 2020

Chemistry A European J

View full text Add to dashboard Cite

This work reports on the concise total synthesis of eight natural products of the mugineic acid and avenic acid families (phytosiderophores). An innovative „east‐to‐west“ assembly of the trimeric products resulted in a high degree of divergence enabling the formation of the final products in just 10 or 11 steps each with a minimum of overall synthetic effort. Chiral pool starting materials (l‐malic acid, threonines) were employed for the outer building blocks while the middle building blocks were accessed by diastereo‐ and enantioselective methods. A highlight of this work consists in the straightforward preparation of epimeric hydroxyazetidine amino acids, useful building blocks on their own, enabling the first synthesis of 3’’‐hydroxymugineic acid and 3’’‐hydroxy‐2’‐deoxymugineic acid.

show abstract

“…Therefore, Professor Nishizawa and colleagues reported that by introducing the mugineic acid biosynthesis gene of barley into rice, rice obtained an MA secretory capacity and exhibited excellent alkaline tolerance, equivalent to that of barley. 13) Inspired by this pioneering report, we considered that an external addition of DMA-Fe(III) complex as a fertilizer may enable rice and corn to grow even in alkaline soil. (Fig.…”

Section: Practical Research Using Mugineic Acidsmentioning

confidence: 99%

“…MA and DMA are characterized by a structure in which Lazetidine-2-carboxylic acid, aspartic acid, and malic acid unit are reductively connected, respectively. Although many synthetic studies of MA and DMA have been reported so far, 14,15) we have developed the following practical synthetic method of DMA production based on a concept that limits 1) the use of amino acid protecting groups as far as possible, and 2) the isolation and purification of each synthetic intermediate.…”

Section: Practical Research Using Mugineic Acidsmentioning

confidence: 99%

Organic Chemistry Research on the Mechanistic Elucidation of Iron Acquisition in Barley

Namba

Murata

2018

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

An organic chemistry approach to the mechanistic elucidation of iron acquisition in graminaceous plants is introduced here. To elucidate this detailed mechanism using phytosiderophores, the efficient synthesis of 2′-deoxymugineic acid (DMA), a phytosiderophore of rice, was established. The synthetic DMA was confirmed to have similar iron transport activity to that of natural mugineic acid (MA). It was also revealed that the addition of synthetic DMA, along with iron, to a rice hydroponic solution enabled the rice to grow well even under an alkaline condition, and DMA clearly showed its high potential as a fertilizer to improve food production. On the other hand, the 2′-hydroxy group of MA was confirmed to serve as a point of introduction for labeling, allowing the synthesis of various mugineic acid derivatives as molecular probes. The incorporation of fluorescent mugineic acid into cells allowed them to be clearly observed by fluorescence confocal analysis, and this provided the first direct experimental evidence of transporter-mediated internalization of mugineic acid into cells.

show abstract

A short practical synthesis of 2′-deoxymugineic acid

Cited by 34 publications

References 15 publications

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

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

A Unified Approach to Phytosiderophore Natural Products

Organic Chemistry Research on the Mechanistic Elucidation of Iron Acquisition in Barley

Contact Info

Product

Resources

About