Mugineic acid

Last updated
Mugineic acid
MugineicAcid.svg
Identifiers
3D model (JSmol)
ChEBI
PubChem CID
UNII
  • InChI=1S/C12H20N2O8/c15-7(11(19)20)1-3-13-9(12(21)22)8(16)5-14-4-2-6(14)10(17)18/h6-9,13,15-16H,1-5H2,(H,17,18)(H,19,20)(H,21,22)/t6-,7-,8-,9-/m0/s1
    Key: GJRGEVKCJPPZIT-JBDRJPRFSA-N
  • C1CN([C@@H]1C(=O)O)C[C@@H]([C@@H](C(=O)O)NCC[C@@H](C(=O)O)O)O
Properties
C12H20N2O8
Molar mass 320.298 g·mol−1
Appearancewhite solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Mugineic acid is the organic compound consisting of a azetidine group and three carboxylates. A colorless solid, it is a siderophore. More specifically, it is a phytosiderophore, i.e. a plant-produced siderophore. It functions as an iron accumulating agent for barley and other plants. Related phytosiderophores include nicotianamine and avenic acid. [1]

Structure of Co(III) complex of tetra-deprotonated mugineic acid (as sodium salt, not shown). BAVJOX11.png
Structure of Co(III) complex of tetra-deprotonated mugineic acid (as sodium salt, not shown).

It is biosynthesized from S-methylmethionine. The compound binds metal ions as a hexadentate ligand. [4]

Related Research Articles

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<span class="mw-page-title-main">Iron(III) fluoride</span> Chemical compound

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<span class="mw-page-title-main">Hydroxamic acid</span> Organic compounds of the form –C(=O)N(OH)–

In organic chemistry, hydroxamic acids are a class of organic compounds bearing the functional group R−C(=O)−N(OH)−R', with R and R' as organic residues. They are amides wherein the nitrogen center has a hydroxyl substituent. They are often used as metal chelators.

<span class="mw-page-title-main">Enterobactin</span> Chemical compound

Enterobactin is a high affinity siderophore that acquires iron for microbial systems. It is primarily found in Gram-negative bacteria, such as Escherichia coli and Salmonella typhimurium.

<span class="mw-page-title-main">Ken Raymond</span> American inorganic chemist

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<span class="mw-page-title-main">Ferrichrome</span> Chemical compound

Ferrichrome is a cyclic hexa-peptide that forms a complex with iron atoms. It is a siderophore composed of three glycine and three modified ornithine residues with hydroxamate groups [-N(OH)C(=O)C-]. The 6 oxygen atoms from the three hydroxamate groups bind Fe(III) in near perfect octahedral coordination.

<span class="mw-page-title-main">Thujaplicin</span> Chemical compound

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Siderocalin(Scn), lipocalin-2, NGAL, 24p3 is a mammalian lipocalin-type protein that can prevent iron acquisition by pathogenic bacteria by binding siderophores, which are iron-binding chelators made by microorganisms. Iron serves as a key nutrient in host-pathogen interactions, and pathogens can acquire iron from the host organism via synthesis and release siderophores such as enterobactin. Siderocalin is a part of the mammalian defence mechanism and acts as an antibacterial agent. Crystallographic studies of Scn demonstrated that it includes a calyx, a ligand-binding domain that is lined with polar cationic groups. Central to the siderophore/siderocalin recognition mechanism are hybrid electrostatic/cation-pi interactions. To evade the host defences, pathogens evolved to produce structurally varied siderophores that would not be recognized by siderocalin, allowing the bacteria to acquire iron.

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<span class="mw-page-title-main">Transition metal thioether complex</span>

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<span class="mw-page-title-main">Transition metal carboxylate complex</span> Class of chemical compounds

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<span class="mw-page-title-main">Rhizoferrin</span> Chemical compound

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<span class="mw-page-title-main">Petrobactin</span> Chemical compound

Petrobactin is a bis-catechol siderophore produced by M. hydrocarbonoclasticus, A. macleodii, and the anthrax-producing B. anthracis. Like other siderophores petrobactin is a highly specific iron(III) transport ligand, contributing to the marine microbial uptake of environmental iron.

References

  1. Prasad, Rajendra; Shivay, Yashbir S.; Kumar, Dinesh (2014). Agronomic Biofortification of Cereal Grains with Iron and Zinc. Advances in Agronomy. Vol. 125. pp. 55–91. doi:10.1016/B978-0-12-800137-0.00002-9. ISBN   9780128001370.
  2. Marsh, Richard E.; Clemente, Dore Augusto (2007). "A survey of crystal structures published in the Journal of the American Chemical Society". Inorganica Chimica Acta. 360 (14): 4017–4024. doi:10.1016/j.ica.2007.02.050.
  3. Mino, Yoshiki; Ishida, Toshimasa; Ota, Nagayo; Inoue, Masatoshi; Nomoto, Kyosuke; Takemoto, Tsunematsu; Tanaka, Hisashi; Sugiura, Yukio (1983). "Mugineic Acid-Iron(III) Complex and its Structurally Analogous Cobalt(III) Complex: Characterization and Implication for Absorption and Transport of Iron in Gramineous Plants". Journal of the American Chemical Society. 105 (14): 4671–4676. doi:10.1021/ja00352a024.
  4. Sugiura, Yukio; Tanaka, Hisashi; Mino, Yoshiki; Ishida, Toshimasa; Ota, Nagayo; Inoue, Masatoshi; Nomoto, Kyosuke; Yoshioka, Himeko; Takemoto, Tsunematsu (1981). "Structure, Properties, and Transport Mechanism of Iron(III) Complex of Mugineic Acid, a Possible Phytosiderophore". Journal of the American Chemical Society. 103 (23): 6979–6982. doi:10.1021/ja00413a043.