Nicotianamine

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Nicotianamine
Names
Systematic IUPAC name
(2S)-1-[(3S)-3-{[(3S)-3-Amino-3-carboxypropyl]amino}-3-carboxypropyl]azetidine-2-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • 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
  • C1CN([C@@H]1C(=O)O)CC[C@@H](C(=O)O)NCC[C@@H](C(=O)O)N
Properties
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).

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.
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