Nicotianamine

Nicotianamine
Names
	Systematic IUPAC name (2S)-1-[(3S)-3-{[(3S)-3-Amino-3-carboxypropyl]amino}-3-carboxypropyl]azetidine-2-carboxylic acid
Identifiers
CAS Number	34441-14-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17721;
ChemSpider	8058557;
PubChem CID	7705;
UNII	2OGX6YHQ1F ;
CompTox Dashboard (EPA)	DTXSID8037677 ;
	InChI InChI=1S/C12H21N3O6/c13-7(10(16)17)1-4-14-8(11(18)19)2-5-15-6-3-9(15)12(20)21/h7-9,14H,1-6,13H2,(H,16,17)(H,18,19)(H,20,21)/t7-,8-,9-/m0/s1 Key: KRGPXXHMOXVMMM-CIUDSAMLSA-N;
	SMILES C1CN([C@@H]1C(=O)O)CC[C@@H](C(=O)O)NCC[C@@H](C(=O)O)N;
Properties
Chemical formula	C12H21N3O6
Molar mass	303.31164 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Nicotianamine is a metal-chelating molecule ubiquitous in higher plants.^[1] It is also used as a precursor for the synthesis of phytosiderophores which play a key role in iron uptake from the soil in graminaceous plants.^[2] Biochemically, it is synthesized by the enzyme nicotianamine synthase, which uses three molecules of S-adenosylmethionine.^[3]

References

^ 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.
^ Mineral Nutrition in Higher Plants, 3rd Edition. ISBN 978-0-12-384905-2
^ Zheng L, Cheng Z, Ai C, Jiang X, Bei X, Zheng Y, Glahn RP, Welch RM, Miller DD, Lei XG, Shou H (2010). "Nicotianamine, a novel enhancer of rice iron bioavailability to humans". PLOS ONE. 5 (4): e10190. Bibcode:2010PLoSO...510190Z. doi:10.1371/journal.pone.0010190. PMC 2855712. PMID 20419136.

[Takahashi_2003-1] 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.

[Marschner_2012-2] Mineral Nutrition in Higher Plants, 3rd Edition. ISBN 978-0-12-384905-2

[Zheng_2010-3] Zheng L, Cheng Z, Ai C, Jiang X, Bei X, Zheng Y, Glahn RP, Welch RM, Miller DD, Lei XG, Shou H (2010). "Nicotianamine, a novel enhancer of rice iron bioavailability to humans". PLOS ONE. 5 (4): e10190. Bibcode:2010PLoSO...510190Z. doi:10.1371/journal.pone.0010190. PMC 2855712. PMID 20419136.

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