Issue 16, 2015

An efficient solid-phase strategy for total synthesis of naturally occurring amphiphilic marine siderophores: amphibactin-T and moanachelin ala-B

Abstract

Microorganisms such as bacteria, fungi and some plants secrete an abundance of suites of low molecular weight, high-affinity iron(III)-chelating acylated siderophores. The peptide composition of a suite of amphiphilic siderophores generated by a Vibrio species, isolated from oligotrophic open ocean water, contained the same iron(III)-scavenging polar head group and is attached to a fatty acid. In the present study, we report the first total synthesis of the naturally obtainable marine siderophores amphibactin-T and moanachelin ala-B on solid-phase using standard Fmoc-chemistry. Furthermore, we discuss the preparation of orthogonal protected Orn amino acid ‘Nα-Fmoc-Nδ-(acetyl)-Nδ-(benzoyloxy)-ornithine’ [Fmoc-Orn(Ac,OBz)-OH], which is the most important constructive building block for amphibactin and moanachelin siderophores syntheses. The applications of this Orn unit on solid-phase have also been discussed.

Graphical abstract: An efficient solid-phase strategy for total synthesis of naturally occurring amphiphilic marine siderophores: amphibactin-T and moanachelin ala-B

Supplementary files

Article information

Article type
Paper
Submitted
19 Jan 2015
Accepted
09 Mar 2015
First published
10 Mar 2015

Org. Biomol. Chem., 2015,13, 4760-4768

Author version available

An efficient solid-phase strategy for total synthesis of naturally occurring amphiphilic marine siderophores: amphibactin-T and moanachelin ala-B

P. Cherkupally, S. Ramesh, T. Govender, H. G. Kruger, B. G. de la Torre and F. Albericio, Org. Biomol. Chem., 2015, 13, 4760 DOI: 10.1039/C5OB00100E

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