Iron(III)-templated macrolactonization of trihydroxamate siderophores.
A method was developed to synthesize macrocyclic trihydroxamate siderophores using optimized Yamaguchi macrolactonization conditions. The natural ability of siderophores to bind iron(III) was exploited to template the reactions and allowed for rapid reaction rates, high product conversions, and the formation of large macrolactone rings up to 35 atoms. An X-ray structure of a 33-membered macrolactone siderophore-Fe(III) complex is presented.
Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556, USA.
Timothy A
TA
Wencewicz
Allen G
AG
Oliver
Marvin J
MJ
Miller
D018360:Crystallography, X-Ray; D005290:Ferric Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D006877:Hydroxamic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007501:Iron / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D017262:Siderophores / Q000138:chemical synthesis* / Q000737:chemistry
D005290:Ferric Compounds; D006877:Hydroxamic Acids; D007783:Lactones; D047028:Macrocyclic Compounds; D017262:Siderophores; D007501:Iron