Mugineic acid

Mugineic acid
Identifiers
CAS Number	69199-37-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:25426;
ChemSpider	9242305;
KEGG	C15500;
PubChem CID	11067153;
UNII	KR256JY76I;
CompTox Dashboard (EPA)	DTXSID90988904 ;
	InChI 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;
	SMILES C1CN([C@@H]1C(=O)O)C[C@@H]([C@@H](C(=O)O)NCC[C@@H](C(=O)O)O)O;
Properties
Chemical formula	C12H20N2O8
Molar mass	320.298 g·mol−1
Appearance	white solid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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]

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

Biosynthesis

Mugineic acid is a derivative of the nicotianamine, a metal-chelating molecule ubiquitous in higher plants that is produced from three molecules of S-adenosyl methionine by the enzyme nicotianamine synthase.^[5]^[6]

The immediate precursor is 2'-deoxymugineic acid which is produced from nicotianamine by two reactions, catalysed by nicotianamine aminotransferase^[7] and 3''-deamino-3''-oxonicotianamine reductase.^[8]

nicotianamine

Two enzymes

2'-deoxymugineic acid

This is followed by insertion of another hydroxyl group, catalysed by the alpha-ketoglutarate-dependent hydroxylase, 2'-deoxymugineic-acid 2'-dioxygenase:^[9]

2'-deoxymugineic acid

2'-dioxygenase

[O]

mugineic acid

Mugineic acid is also used as a precursor for the synthesis of other phytosiderophores which play a key role in iron uptake from the soil in graminaceous plants.^[10]

References

^ 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.
^ 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.
^ 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. Bibcode:1983JAChS.105.4671M. doi:10.1021/ja00352a024.
^ 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. Bibcode:1981JAChS.103.6979S. doi:10.1021/ja00413a043.
^ Takahashi M, Terada Y, Nakai I, Nakanishi H, Yoshimura E, Mori S, Nishizawa NK (2003). "Role of nicotianamine in the intracellular delivery of metals and plant reproductive development". The Plant Cell. 15 (6): 1263–80. doi:10.1105/tpc.010256. PMC 156365. PMID 12782722.
^ Higuchi, Kyoko; Kanazawa, Kenji; Nishizawa, Naoko-Kishi; Chino, Mitsuo; Mori, Satoshi (1994). "Purification and characterization of nicotianamine synthase from Fe-deficient barley roots". Plant and Soil. 165 (2): 173–179. doi:10.1007/BF00008059.
^ Takahashi, Michiko; Yamaguchi, Hirotaka; Nakanishi, Hiromi; Shioiri, Takayuki; Nishizawa, Naoko-Kishi; Mori, Satoshi (1999). "Cloning Two Genes for Nicotianamine Aminotransferase, a Critical Enzyme in Iron Acquisition (Strategy II) in Graminaceous Plants". Plant Physiology. 121 (3): 947–956. doi:10.1104/pp.121.3.947. PMC 59459. PMID 10557244.
^ Shojima, Shinsuke; Nishizawa, Naoko-Kishi; Fushiya, Shinji; Nozoe, Shigeo; Irifune, Tomohiro; Mori, Satoshi (1990). "Biosynthesis of Phytosiderophores". Plant Physiology. 93 (4): 1497–1503. doi:10.1104/pp.93.4.1497. PMC 1062701. PMID 16667646.
^ Kobayashi, Takanori; Nakanishi, Hiromi; Takahashi, Michiko; Kawasaki, Shinji; Nishizawa, Naoko-Kishi; Mori, Satoshi (2001). "In vivo evidence that Ids3 from Hordeum vulgare encodes a dioxygenase that converts 2′-deoxymugineic acid to mugineic acid in transgenic rice". Planta. 212 (5–6): 864–871. doi:10.1007/s004250000453. PMID 11346963.
^ Marschner, Horst (2012). Marschner's Mineral Nutrition of Higher Plants. London Waltham, MA: Academic Press. ISBN 978-0-12-384905-2.

[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. Bibcode:1983JAChS.105.4671M. 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. Bibcode:1981JAChS.103.6979S. doi:10.1021/ja00413a043.

[Takahashi2003-5] Takahashi M, Terada Y, Nakai I, Nakanishi H, Yoshimura E, Mori S, Nishizawa NK (2003). "Role of nicotianamine in the intracellular delivery of metals and plant reproductive development". The Plant Cell. 15 (6): 1263–80. doi:10.1105/tpc.010256. PMC 156365. PMID 12782722.

[6] Higuchi, Kyoko; Kanazawa, Kenji; Nishizawa, Naoko-Kishi; Chino, Mitsuo; Mori, Satoshi (1994). "Purification and characterization of nicotianamine synthase from Fe-deficient barley roots". Plant and Soil. 165 (2): 173–179. doi:10.1007/BF00008059.

[7] Takahashi, Michiko; Yamaguchi, Hirotaka; Nakanishi, Hiromi; Shioiri, Takayuki; Nishizawa, Naoko-Kishi; Mori, Satoshi (1999). "Cloning Two Genes for Nicotianamine Aminotransferase, a Critical Enzyme in Iron Acquisition (Strategy II) in Graminaceous Plants". Plant Physiology. 121 (3): 947–956. doi:10.1104/pp.121.3.947. PMC 59459. PMID 10557244.

[8] Shojima, Shinsuke; Nishizawa, Naoko-Kishi; Fushiya, Shinji; Nozoe, Shigeo; Irifune, Tomohiro; Mori, Satoshi (1990). "Biosynthesis of Phytosiderophores". Plant Physiology. 93 (4): 1497–1503. doi:10.1104/pp.93.4.1497. PMC 1062701. PMID 16667646.

[9] Kobayashi, Takanori; Nakanishi, Hiromi; Takahashi, Michiko; Kawasaki, Shinji; Nishizawa, Naoko-Kishi; Mori, Satoshi (2001). "In vivo evidence that Ids3 from Hordeum vulgare encodes a dioxygenase that converts 2′-deoxymugineic acid to mugineic acid in transgenic rice". Planta. 212 (5–6): 864–871. doi:10.1007/s004250000453. PMID 11346963.

[Marschner2012-10] Marschner, Horst (2012). Marschner's Mineral Nutrition of Higher Plants. London Waltham, MA: Academic Press. ISBN 978-0-12-384905-2.

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