Nicotianamine

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
KEGG
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).
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]

Biosynthesis

The enzyme nicotianamine synthase converts three units of its substrate, S-adenosyl methionine, into nicotianamine and three units of 5′-methylthioadenosine as a by-product.[4]

3
 
S-Adenosyl methionine
 
 
 
 
 
 
3
 
5′-Methylthioadenosine
+
 
Nicotianamine

Metabolism

Nicotianamine binds efficiently to iron II but much less well to the iron III mainly found in soil.[2]: 199  Plants convert it into other phytosiderophores which are more efficient in scavenging iron III and other ions. For example, the enzymes nicotianamine aminotransferase (NAAT)[5] and 3''-deamino-3''-oxonicotianamine reductase (DOR)[6] give two additional compounds:

nicotianamine
 
NAAT
 
 
 
 
 
3"-deamino-3"-oxonicotianamine
DOR
 
 
 
 
 
2'-deoxymugineic acid

Further additions of hydroxyl groups, catalysed by alpha-ketoglutarate-dependent hydroxylases, convert 2'-deoxymugineic acid to mugineic acid and related phytosiderophores.[1][2][7]

References

  1. ^ a b Takahashi, Michiko; Terada, Yasuko; Nakai, Izumi; et al. (2003). "Role of Nicotianamine in the Intracellular Delivery of Metals and Plant Reproductive Development". The Plant Cell. 15 (6): 1263–1280. doi:10.1105/tpc.010256. PMC 156365. PMID 12782722.
  2. ^ a b c Marschner, Horst (2012). Marschner's Mineral Nutrition of Higher Plants. London Waltham, MA: Academic Press. 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.
  4. ^ Higuchi, Kyoko; Kanazawa, Kenji; Nishizawa, Naoko-Kishi; Chino, Mitsuo; Mori, Satoshi (1994). "Purification and characterization of nicotianamine synthase from Fe-deficient barley roots". Plant and Soil. 165 (2): 173–179. doi:10.1007/BF00008059.
  5. ^ Takahashi, Michiko; Yamaguchi, Hirotaka; Nakanishi, Hiromi; et al. (1999). "Cloning Two Genes for Nicotianamine Aminotransferase, a Critical Enzyme in Iron Acquisition (Strategy II) in Graminaceous Plants". Plant Physiology. 121 (3): 947–956. doi:10.1104/pp.121.3.947. PMC 59459. PMID 10557244.
  6. ^ Shojima, Shinsuke; Nishizawa, Naoko-Kishi; Fushiya, Shinji; et al. (1990). "Biosynthesis of Phytosiderophores". Plant Physiology. 93 (4): 1497–1503. doi:10.1104/pp.93.4.1497. PMC 1062701. PMID 16667646.
  7. ^ Kobayashi, Takanori; Nakanishi, Hiromi; Takahashi, Michiko; Kawasaki, Shinji; Nishizawa, Naoko-Kishi; Mori, Satoshi (2001). "In vivo evidence that Ids3 from Hordeum vulgare encodes a dioxygenase that converts 2′-deoxymugineic acid to mugineic acid in transgenic rice". Planta. 212 (5–6): 864–871. doi:10.1007/s004250000453. PMID 11346963.
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