74235-24-8

Basic information

• Product Name: 2Deoxymugineic Acid
• Synonyms: (αS,2S)-2-Carboxy-α-[[(3S)-3-carboxy-3-hydroxypropyl]aMino]-1-azetidinebutanoic Acid;2'-DehydroxyMugineic Acid
• CAS NO: 74235-24-8
• Molecular Formula: C12H20N2O7
• Molecular Weight: 304.297
• Product Categories: Amino Acids & Derivatives;Chelating Agents & Ligands
• Mol File: 74235-24-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 653.1°C at 760 mmHg
• Flash Point: 348.8°C
• Appearance: /
• Density: 1.468g/cm³
• Vapor Pressure: 8.02E-20mmHg at 25°C
• Refractive Index: 1.578
• PKA: 2.07±0.10(Predicted)
• CAS DataBase Reference: 2Deoxymugineic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2Deoxymugineic Acid(74235-24-8)
• EPA Substance Registry System: 2Deoxymugineic Acid(74235-24-8)

Safety Data

• Hazardous Substances Data: 74235-24-8(Hazardous Substances Data)

Usage

Description

2Deoxymugineic Acid is a phytosiderophore, an iron-chelating amino acid produced in higher plants to promote the uptake of iron from the soil.

Uses

Used in Plant Nutrition:
2Deoxymugineic Acid is used as an iron chelator for enhancing iron uptake in plants. It plays a crucial role in the process of acquiring iron from the soil, which is essential for various metabolic processes and overall plant growth and development.

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

Upstream product

• 958350-41-9 C₂₄H₄₄N₂O₇ 
• 159848-85-8 (3S,3'S)-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane 
• 159848-87-0 (3S,3'S)-3-<3'-acetoxy-N-tert-butoxycarbonyl-3'-(4-methoxyphenyl)propylamino>-3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane 
• 159848-86-9 (3S,3'S)-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane 
• 159848-89-2 tert-butyl (2S,3'S)-2-(3'-acetoxy-N-tert-butoxycarbonyl-3'-tert-butoxycarbonylpropylamino)-4-(2,2,2-trichloroethoxycarbonyloxy)butanoate 
• 159848-83-6 methyl (3S,3'S)-3--3-(4-methoxyphenyl)propionate 
• 159848-84-7 [(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-phenyl)-propyl]-[(S)-3-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid tert-butyl ester 
• 159848-88-1 (S)-2-[((S)-3-Acetoxy-3-carboxy-propyl)-tert-butoxycarbonyl-amino]-4-(2,2,2-trichloro-ethoxycarbonyloxy)-butyric acid 
• 159848-82-5 methyl (3S,3'S)-3-<3'-tert-butyldimethylsiloxy-3'-(4-methoxyphenyl)propylamino>-3-(4-methoxyphenyl)propionate 
• 159848-90-5 tert-butyl (2S,3'S)-2-(3'-acetoxy-N-tert-butoxycarbonyl-3'-tert-butoxycarbonylpropylamino)-4-hydroxybutanoate 
• 159848-91-6 tert-butyl (2S,3'S)-2-(3'-acetoxy-N-tert-butoxycarbonyl-3'-tert-butoxycarbonylpropylamino)-4-oxobutanoate 
• 201283-57-0 (2S,3S,3''S)-N-[3-(3-acetoxy-3-methoxycarbonylpropanethioamido)-3-t-butoxycarbonylpropanethioyl]azetidine-2-carboxylic acid t-butyl ester 
• 201283-56-9 (2S,3S,3''S)-N-[3-(3-acetoxy-3-methoxycarbonylpropanamido)-3-t-butoxycarbonylpropanoyl]azetidine-2-carboxylic acid t-butyl ester 
• 860795-17-1 (S)-1-{(S)-3-Benzyloxycarbonyl-3-[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propylamino]-propyl}-azetidine-2-carboxylic acid 

Relevant articles and documents

A Unified Approach to Phytosiderophore Natural Products

This work reports on the concise total synthesis of eight natural products of the mugineic acid and avenic acid families (phytosiderophores). An innovative ?east-to-west“ assembly of the trimeric products resulted in a high degree of divergence enabling the formation of the final products in just 10 or 11 steps each with a minimum of overall synthetic effort. Chiral pool starting materials (l-malic acid, threonines) were employed for the outer building blocks while the middle building blocks were accessed by diastereo- and enantioselective methods. A highlight of this work consists in the straightforward preparation of epimeric hydroxyazetidine amino acids, useful building blocks on their own, enabling the first synthesis of 3’’-hydroxymugineic acid and 3’’-hydroxy-2’-deoxymugineic acid.

A practical synthesis of the phytosiderophore 2′-deoxymugineic acid: A key to the mechanistic study of iron acquisition by graminaceous plants

(Chemical Equation Presented) Ironing out plant uptake: The phytosiderophores mugineic acid (MA) and deoxymugineic acid (DMA) were synthesized in a few steps with minimum use of protecting groups and workup/purification procedures (see scheme; Boc: tert-butoxycarbonyl) and their potencies in transporter-mediated iron(III) acquisition were tested. The sufficient supply of these compounds will enable study of the molecular mechanism of iron acquisition and utilization by graminaceous plants.

Expeditious synthesis of nicotianamine and 2′-deoxymugineic acid

A simple and efficient method of synthesizing nicotianamine 4 and 2′-deoxymugineic acid 3 was devised. We employed thioamide as an intermediate and the title compounds (4 and 3) were afforded via chemoselective reduction of the thioamides in 33% overall yield through 7 steps and 30% overall yield through 8 steps, respectively.