An efficient solid-phase strategy for total synthesis of naturally occurring amphiphilic marine siderophores: amphibactin-T and moanachelin ala-B
| Autor: | Fernando Albericio, Beatriz G. de la Torre, Prabhakar Cherkupally, Thavendran Govender, Suhas Ramesh, Hendrik G. Kruger |
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| Rok vydání: | 2015 |
| Předmět: |
Ornithine
Siderophore Stereochemistry Iron Oceans and Seas Microorganism Siderophores Peptide Biochemistry Amphiphile Amino Acids Organic Chemicals Physical and Theoretical Chemistry Chromatography High Pressure Liquid Chelating Agents Vibrio chemistry.chemical_classification Molecular Structure biology Fatty Acids Organic Chemistry Total synthesis Fatty acid biology.organism_classification Amino acid Molecular Weight chemistry Drug Design Peptides Water Microbiology Oligopeptides Bacteria |
| Zdroj: | Organic & Biomolecular Chemistry. 13:4760-4768 |
| ISSN: | 1477-0539 1477-0520 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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