83966-23-8Relevant articles and documents
Convergent Synthesis of Macrocyclic and Linear Desferrioxamines
Chiu, Cheng-Hsin,Chung, Wen-Sheng,Jheng, Ting-Cian,Mong, Kwok-Kong Tony,Peng, Bo-Chun
, (2020/06/17)
Polyhydroxamate desferrioxamines (DFO) are nontoxic siderophores endowed with high potential for development of therapeutic chelating agents. Herein, we report a modular and convergent strategy for diverse synthesis of macrocyclic and linear DFOs. The strategy employed orthogonally protected N-hydroxy-N-succinylcadaverine building blocks, which allowed bidirectional extension of the DFO structure. The efficiency of the new strategy was demonstrated by the total synthesis of 44-membered macrocyclic DFO-T1, as well as four related DFO compounds in 11–13 linear steps and 2.1 %–10 % overall yields. Comparison of the iron binding affinity of the DFOs revealed DFO-E as the best chelator.
Method for the synthesis of desferrioxamine B and analogs thereof
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, (2008/06/13)
Disclosed is a synthesis of desferrioxamine B and analogs and homologs thereof beginning with the generation of the O-protected N-(4-cyanobutyl)hydroxylamine which is acylated at the O-benzylhydroxylamine nitrogen with either succinic or acetic anhydride. The resulting half-acid amide or amide respectively, is subjected to a series of high yield condensations and reductions which provide desferrioxamine B in 45% overall yield. Finally, a desamino analog of desferrioxamine is prepared in order to demonstrate the synthetic utility of the scheme as applied to desferrioxamine derivatives.
Artificial Siderophores. 1. Synthesis and Microbial Iron Transport Capabilities
Lee, Byung Hyun,Miller, Marvin J.,Prody, Catherine A.,Neilands, John B.
, p. 317 - 323 (2007/10/02)
Several di- and trihydroxamate analogues of natural microbial iron chelators have been prepared.The syntheses involved linkage of core structural units, including pyridinedicarboxylic acid, benzenetricarboxylic acid, nitrilotriacetic acid, and tricarballylic acid, by amide bonds to 1-amino-ω-(hydroxyamino)alkanes to provide the polyhydroxamates 1-5.The required protected (hydroxyamino)alkanes 8, 16, and 21 were prepared by different routes. 1-Amino-3-propane di-p-toluenesulfonate (8) was prepared from the N-protected aminopropanol 6 by oxidation to the aldehyde, formation of the substituted oxime, and reduction with NaBH3CN followed by deprotection of the Boc group.The pentyl derivatives 16 and 21 were made by direct alkylation with either benzyl acetohydroxamate or N-carbobenzoxy-O-benzylhydroxylamine.In Escherichia coli RW193 most of the analogues behaved nutritionally as ferrichrome.However, in E. coli AN193, a mutant lacking the ferrichrome receptor, capacity to use other natural siderophores was retained while response to all analogues was lost.
