Total synthesis of the siderophore danoxamine

J Org Chem. 2000 Aug 11;65(16):4833-8. doi: 10.1021/jo000050m.

Abstract

The total synthesis of the linear trihydroxamate siderophore, Danoxamine, is described. Danoxamine is a siderophore component of the naturally occurring siderophore-drug conjugates Salmycin A-D. The synthesis of Danoxamine features a series of coupling reactions involving N-(5-benzyloxypentyl)-O-benzylhydroxylamine being linked by a succinoyl linker to N-(benzyloxy)-1,5-pentanediamine. Two more succinoyl linkers and another N-(benzyloxy)-1,5-pentanediamine were used in coupling reactions to afford the fully protected siderophore. The linear tetrabenzyl-protected trihydroxamate was deprotected to afford the natural product Danoxamine.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Hydroxamic Acids / chemical synthesis*
  • Hydroxamic Acids / metabolism
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Siderophores / chemical synthesis*
  • Spectrometry, Mass, Fast Atom Bombardment

Substances

  • Hydroxamic Acids
  • Siderophores