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  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17721
ChemSpider	8058557
PubChem CID	9882882
UNII	2OGX6YHQ1F  Y
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

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