Nicotianamine
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| Systematic IUPAC name
(2S)-1-[(3S)-3-{[(3S)-3-Amino-3-carboxypropyl]amino}-3-carboxypropyl]azetidine-2-carboxylic acid | |
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| 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).
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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]
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:
![2D representation of the chemical structure of Q27117402.](#/media/File:3"-deamino-3"'-oxonicotianamine.svg)
Further additions of hydroxyl groups, catalysed by alpha-ketoglutarate-dependent hydroxylases, convert 2'-deoxymugineic acid to mugineic acid and related phytosiderophores.[1][2][7]