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

• Published in: Organic & biomolecular chemistry Vol. 13; no. 16; pp. 4760 - 4768
• Main Authors: Cherkupally, Prabhakar, Ramesh, Suhas, Govender, Thavendran, Kruger, Hendrik G., de la Torre, Beatriz G., Albericio, Fernando
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 28.04.2015
• Subjects: Amino Acids - chemistry; Chelating Agents - chemistry; Chemistry; Chemistry, Organic; Chromatography, High Pressure Liquid; Drug Design; Fatty Acids - chemistry; Iron - chemistry; Molecular Structure; Molecular Weight; Oceans and Seas; Oligopeptides - chemical synthesis; Organic Chemicals; Ornithine - chemistry; Peptides - chemistry; Physical Sciences; Science & Technology; Siderophores - chemistry; Vibrio - metabolism; Water Microbiology; SUITE; HYDROXYORNITHINE; PEPTIDES; LIGANDS; AFFINITY; BACTERIUM; N5-ACETYL-N5-HYDROXY-L-ORNITHINE; RHODOTORULIC ACID; IRON ACQUISITION; HYDROXY-L-ORNITHINE
• 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 'Na(alpha)Fmoc-N-delta-(acetyl)-N-delta-(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.