Iron(III)-templated macrolactonization of trihydroxamate siderophores

Timothy A. Wencewicz; Allen G. Oliver; Marvin J. Miller

doi:10.1021/ol301869x

Iron(III)-templated macrolactonization of trihydroxamate siderophores

Timothy A. Wencewicz
, Allen G. Oliver
, Marvin J. Miller

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	4390-4393
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	17
DOIs	https://doi.org/10.1021/ol301869x
State	Published - Sep 7 2012

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title = "Iron(III)-templated macrolactonization of trihydroxamate siderophores",

abstract = "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.",

author = "Wencewicz, \{Timothy A.\} and Oliver, \{Allen G.\} and Miller, \{Marvin J.\}",

year = "2012",

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AU - Wencewicz, Timothy A.

AU - Oliver, Allen G.

AU - Miller, Marvin J.

PY - 2012/9/7

Y1 - 2012/9/7

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84866050942

U2 - 10.1021/ol301869x

DO - 10.1021/ol301869x

M3 - Article

C2 - 22906163

AN - SCOPUS:84866050942

SN - 1523-7060

VL - 14

SP - 4390

EP - 4393

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Iron(III)-templated macrolactonization of trihydroxamate siderophores

Abstract

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