- A Unified Approach to Phytosiderophore Natural Products
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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.
- Kratena, Nicolas,G?kler, Tobias,Maltrovsky, Lara,Oburger, Eva,Stanetty, Christian
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supporting information
p. 577 - 580
(2020/11/02)
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- EFFECTIVE PRODUCTION PROCESS FOR MUGINEIC ACID COMPOUND
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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)).
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Page/Page column 13
(2009/10/01)
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- A practical synthesis of the phytosiderophore 2′-deoxymugineic acid: A key to the mechanistic study of iron acquisition by graminaceous plants
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(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.
- Namba, Kosuke,Murata, Yoshiko,Horikawa, Manabu,Iwashita, Takashi,Kusumoto, Shoichi
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p. 7060 - 7063
(2008/09/18)
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- A short practical synthesis of 2′-deoxymugineic acid
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A short and practical synthesis of 2′-deoxymugineic acid (DMA) has been developed via reductive alkylation with the aldehyde intermediates. No protection of azetidine-2-carboxylic acid was required and the presence of free carboxylic acid function facilitated purification by simple acid and base extractions. Furthermore, the intermediates were conveniently purified by HPLC due to the presence of chromophoric benzyl ester protecting group(s). Hydrogenolysis of the benzyl protecting groups in the final step furnished DMA in overall good yield.
- Singh, Satendra,Crossley, George,Ghosal, Saswati,Lefievre, Yann,Pennington, Michael W.
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p. 1419 - 1421
(2007/10/03)
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- Expeditious synthesis of nicotianamine and 2′-deoxymugineic acid
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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.
- Miyakoshi, Katsuhiro,Oshita, Jun,Kitahara, Takeshi
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p. 3355 - 3360
(2007/10/03)
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- A novel synthetic approach towards phytosiderophores: Expeditious synthesis of nicotianamine and 2'-deoxymugineic acid
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A short and a novel approach for synthesis of nicotianamine, 2'- deoxymugineic acid and related phytosiderophores has been achieved through peptide intermediates. Selective amide reduction in the presence of ester functionalities by conversion to thioamid
- Klair, Sukhbinder S.,Mohan, Hindupur R.,Kitahara, Takeshi
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- A new efficient synthesis of nicotianamine and 2′-deoxymugineic acid
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Nicotianamine and 2′-deoxymugineic acid, phytosiderophores, have been efficiently synthesized, which will be suitable for large scale production of these plant physiologically important compounds. The synthetic method for 2′,3″-dideoxy-3″-oxomugineic acid was also investigated.
- Shioiri, Takayuki,Irako, Naoko,Sakakibara, Sachiko,Matsuura, Fumiyoshi,Hamada, Yasumasa
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p. 519 - 530
(2007/10/03)
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- Total Synthesis of 2'-Deoxymugineic Acid and Nicotianamine
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Steroselective total synthesis of the unique phytosiderophores, 2'-deoxymugineic acid (4) and nicotianamine (5), has been achieved from the β-tyrosine derivative 21 using its aryl groups as the carboxyl synthon.
- Matsuura, Fumiyoshi,Hamada, Yasumasa,Shioiri, Takayuki
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p. 9457 - 9470
(2007/10/02)
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- SYNTHESIS OF AVENIC ACID A AND 2'-DEOXYMUGIENIC ACID, AMINO ACIDS POSSESSING AN IRON CHELATING ACTIVITY
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Avenic acid A (1), an amino acid derivative possessing an iron chelating activity and excreted from the root of Avena sativa L. was synthesized in optically active form by successive reductive coupling of protected L-aspartic β-semialdehyde and L-malic semialdehyde with L-homoserine lactone. 2'-Deoxymugineic acid (2), a related substance was also synthesized by the same method by which the stereostructure of this amino acid derivative was proved to be 2(S), 3'(S),3''(S)-N--azetidine-2-carboxylic acid.
- Fushiya, Shinji,Sato, Yoshikazu,Nakatsuyama, Shuichi,Kanuma, Norio,Nozoe, Shigeo
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p. 909 - 912
(2007/10/02)
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