Convergent Synthesis of Macrocyclic and Linear Desferrioxamines

Cheng Hsin Chiu, Ting Cian Jheng, Bo Chun Peng, Wen Sheng Chung, Kwok Kong Tony Mong*

*Corresponding author for this work

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)3650-3659
Number of pages10
JournalEuropean Journal of Organic Chemistry
Volume2020
Issue number24
DOIs
StatePublished - 30 Jun 2020

Keywords

  • Convergent synthesis
  • Desferrioxamines
  • Hydroxamate
  • Iron binding
  • Siderophores

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