69199-37-7

Usage

Definition

ChEBI: An azetidinecarboxylic acid that is the parent of the class of mugineic acids.

InChI:InChI=1/C12H20N2O8/c15-7(11(19)20)1-3-13-9(12(21)22)8(16)5-14-4-2-6(14)10(17)18/h6-9,13,15-16H,1-5H2,(H,17,18)(H,19,20)(H,21,22)

Upstream product

• 1028191-78-7 C₂₄H₄₄N₂O₈ 
• 105762-98-9 (S)-1-[(2S,3S)-3-Benzyloxycarbonyl-3-((R)-3-benzyloxycarbonyl-3-benzyloxymethoxy-propylamino)-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-azetidine-2-carboxylic acid benzyl ester 
• 146565-68-6 tert-butyl (2S,2'S,3'S,3''S)-3'-(3''-tert-butoxycarbonyl-3''-tert-butyldimethylsilyloxypropylamino)-3'-tert-butoxycarbonyl-2'-methoxymethyloxypropyl-2-azetidinecarboxylate 

Relevant academic research and scientific papers

EFFECTIVE PRODUCTION PROCESS FOR MUGINEIC ACID COMPOUND

A method for producing mugineic acids, which is represented by the following scheme: (wherein R1 and R2 represent a hydrogen atom or a hydroxyl group, R3 represents a hydroxyl group or an amino group, R4 and R7 represent a hydrogen atom or a protecting group of a carboxyl group, R5 represents a protecting group of an amino group, R6 represents a protecting group of a carboxyl group, and R8 represents -OR9 (wherein R9 represents a protecting group of a hydroxyl group) or -NHR10 (wherein R10 represents a protecting group of an amino group)).

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.

Total Synthesis of Mugineic Acid. Efficient Use of the Phenyl Group as the Carboxyl Synthon

Stereoselective total synthesis of mugineic acid (1), a unique phytosiderophore from roots of barley, has been achieved from readily available (2S,3S)- and (2R,3R)-2,3-epoxycinnamyl alcohols (5) and (6).The key step is the oxidation of the phenyl group to the carboxylic acid by use of the ruthenium trichloride-sodium metaperiodate system.

Efficient Synthesis of Mugineic Acid, A Typical Phytosiderophore, Utilizing the Phenyl Group as the Carboxyl Synthon

Stereoselective total synthesis of mugineic acid, a unique phytosiderophore from roots of barley, has been achieved from (2R,3R)- and (2S,3S)-2,3-epoxycinnamyl alcohols employing the phenyl group as the carboxyl synthon.

Synthesis of Mugineic Acid through Direct C-Acylation Using Diphenyl Phosphorazidate

The first synthesis of mugineic acid, a typical phytosiderophore from roots of barley, has been achieved through direct C-acylation using diphenyl phosphorazidate (DPPA).