Chemistry:Mugineic acid
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| Properties | |
| 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). | |
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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]
This is followed by insertion of another hydroxyl group, catalysed by the alpha-ketoglutarate-dependent hydroxylase, 2'-deoxymugineic-acid 2'-dioxygenase:[9]
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. 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. doi:10.1021/ja00352a024. Bibcode: 1983JAChS.105.4671M.
- ↑ Sugiura, Yukio; Tanaka, Hisashi; Mino, Yoshiki; Ishida, Toshimasa; Ota, Nagayo; Inoue, Masatoshi; Nomoto, Kyosuke; Yoshioka, Himeko et al. (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. Bibcode: 1981JAChS.103.6979S.
- ↑ "Role of nicotianamine in the intracellular delivery of metals and plant reproductive development". The Plant Cell 15 (6): 1263–80. 2003. doi:10.1105/tpc.010256. 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. 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. 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. https://www.google.co.uk/books/edition/Marschner_s_Mineral_Nutrition_of_Higher/_a-hKcXXQuAC?hl=en&gbpv=1&printsec=frontcover&bsq=mugineic.
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