Mugineic acid

Mugineic acid
Identifiers
CAS Number	69199-37-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:25426;
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]

Structure of Co(III) complex of tetra-deprotonated mugineic acid (as sodium salt, not shown).^[2]^[3]

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

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. 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. doi:10.1021/ja00413a043.

[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.

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[2]

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Identifiers

CAS Number	69199-37-7^N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:25426
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