CAS 74235-24-8

2′-Deoxymugineic acid

Description:

2′-Deoxymugineic acid (CAS 74235-24-8) is a naturally occurring compound classified as a phytosiderophore, primarily produced by certain grasses, including members of the Poaceae family. This compound plays a crucial role in iron acquisition, particularly in environments where iron availability is limited. Structurally, it is characterized by a hydroxylated amino acid backbone, which contributes to its chelating properties, allowing it to form stable complexes with iron ions. This chelation facilitates the uptake of iron by plant roots, enhancing their growth and development in iron-deficient soils. Additionally, 2′-deoxymugineic acid is involved in various physiological processes, including the regulation of plant responses to stress. Its biosynthesis is tightly regulated and influenced by environmental factors, making it an important subject of study in plant physiology and soil chemistry. Overall, 2′-deoxymugineic acid exemplifies the intricate relationship between plants and their environment, particularly in nutrient acquisition strategies.

Formula: C₁₂H₂₀N₂O₇

InChI: InChI=1/C12H20N2O7/c15-9(12(20)21)1-4-13-7(10(16)17)2-5-14-6-3-8(14)11(18)19/h7-9,13,15H,1-6H2,(H,16,17)(H,18,19)(H,20,21)/t7-,8-,9-/m0/s1

InChI key: InChIKey=CUZKLRTTYZOCSD-CIUDSAMLSA-N

SMILES: C(C[C@H](NCC[C@@H](C(O)=O)O)C(O)=O)N1[C@H](C(O)=O)CC1

Synonyms:

• 2′-Dehydroxymugineic acid
• 2′-Deoxymugineic acid
• 1-Azetidinebutanoic acid, 2-carboxy-α-[[(3S)-3-carboxy-3-hydroxypropyl]amino]-, (αS,2S)-
• 1-Azetidinebutanoic acid, 2-carboxy-α-[(3-carboxy-3-hydroxypropyl)amino]-, [2S-[1[αR*(R*)],2R*]]-
• (αS,2S)-2-Carboxy-α-[[(3S)-3-carboxy-3-hydroxypropyl]amino]-1-azetidinebutanoic acid

2'-Deoxymugineic Acid

Controlled Product

CAS: 74235-24-8

Applications Phytosiderophores are produced in higher plants as iron chelating amino acids that promote uptake of iron from soil.
References Klair, S., et al.: J. Plant Nutr., 19, 1295 (1996),

Formula: C₁₂H₂₀N₂O₇

Color and Shape: Neat

Molecular weight: 304.3

Ref: TR-D243250

2'-Deoxymugineic acid

CAS: 74235-24-8

2'-Deoxymugineic acid is a natural product that has been synthesized in the laboratory. It is a structural analogue of the amino acid, L-tryptophan, and has been shown to be a competitive inhibitor of the enzyme, tryptophan synthase. 2'-Deoxymugineic acid also inhibits uptake by plant roots and chloride transport in human cells (caco-2). 2'-Deoxymugineic acid has also been shown to inhibit bacterial growth in vitro by inhibiting protein synthesis.

Formula: C₁₂H₂₀N₂O₇

Purity: Min. 95 Area-%

Color and Shape: Powder

Molecular weight: 304.3 g/mol

Ref: 3D-FD21060