A metal chelator and phytosiderophore precursor
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Nicotianamine

Item No. 19958

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
αS-[[(3S)-3-amino-3-carboxypropyl]amino]-2S-carboxy-1-azetidinebutanoic acid
CAS Number
34441-14-0
Molecular Formula
C12H21N3O6
Formula Weight
303.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: slightly solubleWater: slightly soluble
SMILES
OC([C@@H](NCC[C@H](N)C(O)=O)CCN1[C@H](C(O)=O)CC1)=O
InChi Code
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
InChi Key
KRGPXXHMOXVMMM-CIUDSAMLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $236

    Add

    1 mg

    $400

    Add
    Product Description

    Nicotianamine is a metal chelator and phytosiderophore precursor produced in plants that has a role in the uptake, translocation, and intracellular transport of metals.1 Treating lettuce (L. sativa) with a Cu(OH)2-based pesticide raises nicotianamine levels 12- to 27-fold compared to non-pesticide treated plants.2 Nicotianamine also inhibits rabbit angiotensin-coverting enzyme (ACE) (IC50 = 0.26 μM) and human recombinant ACE2 (IC50 = 84 nM).3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Curie, C., Cassin, G., Couch, D., et al. Metal movement within the plant: Contribution of nicotianamine and yellow stripe 1-like transporters. Ann. Bot. 103(1), 1-11 (2009).

    2. Zhao, L., Ortiz, C., Adeleye, A.S., et al. Metabolomics to detect response of lettuce (Lactuca sativa) to Cu(OH)2 nanopesticides: Oxidative stress response and detoxification mechanisms. Environ. Sci. Technol. 50(17), 9697-9707 (2016).

    3. Kinoshita, E., J., Y., and Kikuchi, M. Purification and identification of an angiotensin I-converting enzyme inhibitor from soy sauce. Biosci. Biotech. Biochem. 57(7), 1107-1110 (1993).

    4. Takahashi, S., Yoshiya, T., Yoshizawa-Kumagaye, K., et al. Nicotianamine is a novel angiotensin-converting enzyme 2 inhibitor in soy-bean. Biomed. Res. (Tokyo) 36(3), 219-224 (2015).