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N2561-80 Nicotianamine CAS: 34441-14-0

Specifications
References
CAS Number
34441-14-0
Grade
Highly Purified
Molecular Formula
C12H21N3O6
Molecular Weight
303.31
EU Commodity Code
38220090
Shipping Temp
RT
Storage Temp
-20°C
(αS,2S)-α-[[(3S)-3-Amino-3-carboxypropyl]amino]-2-carboxy-1-azetidinebutanoic Acid; [2S-[1[αR*(R*)],2R*]]-α-[(3-Amino-3-carboxypropyl)amino]-2-carboxy- 1-azetidinebutanoic Acid

Phytosiderophores are produced in higher plants as iron chelating amino acids that promote uptake of iron from soil. 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 uM) and human recombinant ACE2 (IC50 = 84 nM).3,4

Synonyms
(αS,2S)-α-[[(3S)-3-Amino-3-carboxypropyl]amino]-2-carboxy-1-azetidinebutanoic Acid; [2S-[1[αR*(R*)],2R*]]-α-[(3-Amino-3-carboxypropyl)amino]-2-carboxy- 1-azetidinebutanoic Acid
CAS No
34441-14-0
Molecular Formula
C12H21N3O6
Molecular Weight
303.31
Purity
~90%
Appearance
White to off-white solid
Solubility
Methanol (Slightly), Water (Slightly)
Melting Point
>200°C (dec.)
Method for Determining Identity
Proton NMR (D2O) Spectroscopic and Mass Spectrometric Analysis
TLC Conditions
C18; Methanol: Water = 6:4; Visualized with KMnO4; Single spot, Rf=0.50
Specific Rotation
-37.6º (c=1, Water)
Water Content (Karl Fischer)
~10%
Atmosphere
Inert Gas
Storage and Stability
May be stored at RT for short-term only. Long-term storage is recommended at -20°C. Stable for 6 months after receipt. For maximum recovery of product, centrifuge the original vial prior to removing the cap. Store under inert atmosphere.
References
1. 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). 5. Klair, S., et al.: J. Plant Nutr., 19:1295 (1996)
USBio References
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