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Synthesis 2022; 54(16): 3499-3557
DOI: 10.1055/a-1783-0751
DOI: 10.1055/a-1783-0751
review
Advances in the Synthesis of Enterobactin, Artificial Analogues, and Enterobactin-Derived Antimicrobial Drug Conjugates and Imaging Tools for Infection Diagnosis
This work has been carried out within the framework of the SMART BIOTECS alliance between the Technische Universität Braunschweig and the Leibniz Universität Hannover. This initiative is supported by the Niedersächsisches Ministerium für Wissenschaft und Kultur (Ministry of Science and Culture (MWK) of Lower Saxony, Germany). Financially support by the Deutsche Forschungsgemeinschaft (Grant KL3012/2-1) and Fonds der Chemischen Industrie is gratefully acknowledged. The content of this work is solely the responsibility of the authors and does not necessarily represent the official views of the funding agencies.
In memoriam of Prof. Dr. Dieter Enders
Abstract
Iron is an essential growth factor for bacteria, but although highly abundant in nature, its bioavailability during infection in the human host or the environment is limited. Therefore, bacteria produce and secrete siderophores to ensure their supply of iron. The triscatecholate siderophore enterobactin and its glycosylated derivatives, the salmochelins, play a crucial role for iron acquisition in several bacteria. As these compounds can serve as carrier molecules for the design of antimicrobial siderophore drug conjugates as well as siderophore-derived tool compounds for the detection of infections with bacteria, their synthesis and the design of artificial analogues is of interest. In this review, we give an overview on the synthesis of enterobactin, biomimetic as well as totally artificial analogues, and related drug-conjugates covering up to 12/2021.
1 Introduction
2 Antibiotic Crisis and Sideromycins as Natural Templates for New Antimicrobial Drugs
3 Biosynthesis of Enterobactin, Salmochelins, and Microcins
4 Total Synthesis of Enterobactin and Salmochelins
5 Chemoenzymatic Semi-synthesis of Salmochelins and Microcin E492m Derivatives
6 Synthesis of Biomimetic Enterobactin Derivatives with Natural Tris-lactone Backbone
7 Synthesis of Artificial Enterobactin Derivatives without Tris-lactone Backbone
8 Conclusions
Key words
enterobactin - salmochelins - microcins - siderophores - drug conjugates - catecholates - tris-lactone - iron(III) chelatorPublication History
Received: 15 January 2022
Accepted after revision: 28 February 2022
Accepted Manuscript online:
28 February 2022
Article published online:
17 May 2022
© 2022. Thieme. All rights reserved
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