High-Yield Synthesis of the Enterobactin Trilactone and Evaluation of Derivative Siderophore Analogs1

M Meyer, JR Telford, SM Cohen, DJ White…

Index: Meyer; Telford; Cohen; White; Xu; Raymond Journal of the American Chemical Society, 1997 , vol. 119, # 42 p. 10093 - 10103

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Citation Number: 69

Abstract

A novel one-step synthesis of the macrocyclic triserine trilactone scaffold of the siderophore enterobactin, which eliminates the β-lactonization step of N-tritylserine, is presented. The cyclization reaction is based on a stannoxane template and leads to an overall yield of~ 50%. This enables the practical functionalization of the trilactone by attaching chelating groups other than catecholamides. The conformational stability of the trilactone ring has ...