Total synthesis of the siderophore danoxamine.
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.
Roosenberg
J M
JM
Department of Chemistry & Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556-5670, USA.
Miller
M J
MJ
D006877:Hydroxamic Acids / Q000138:chemical synthesis* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D017262:Siderophores / Q000138:chemical synthesis*; D016339:Spectrometry, Mass, Fast Atom Bombardment
D006877:Hydroxamic Acids; D017262:Siderophores