An efficient solid-phase strategy for total synthesis of naturally occurring amphiphilic marine siderophores: amphibactin-T and moanachelin ala-BElectronic supplementary information (ESI) available: Copies of 1H and 13C NMR, HPLC profiles and HRMS (ESI-QTOF) mass spectrum profiles of intermediates/products. See DOI: 10.1039/c5ob00100e

• Main Authors: Cherkupally, Prabhakar, Ramesh, Suhas, Govender, Thavendran, Kruger, Hendrik G, de la Torre, Beatriz G, Albericio, Fernando
• Format: Article
• Language: English
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c5ob00100e

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 ' N α -Fmoc- N δ -(acetyl)- N δ -(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. The first total synthesis of the naturally obtainable marine siderophores amphibactin-T and moanachelin ala-B on solid-phase using standard Fmoc-chemistry is reported.