Nicotianamine

Nicotianamine
Names

IUPAC name N-(N-(3-amino-3-carboxypropyl)-3-amino-3-carboxypropyl)azetidine-2-carboxylic acid
Identifiers
CAS Number	34441-14-0
ChEBI	CHEBI:17721
ChemSpider	8058557
Jmol 3D model	Interactive image
PubChem	7705
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 an angiotensin I-converting enzyme inhibitor. A metal-chelating molecule, it is ubiquitous in higher plants.^[1] Biochemically, it is synthesized by the enzyme nicotianamine synthase, which uses three molecules of S-adenosylmethionine.^[2]

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.
↑ 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 5 (4): e10190. doi:10.1371/journal.pone.0010190.

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