title: 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 '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.
authors: Catalysis and Peptide Research Unit, School of Health Sciences, University of Kwazulu-Natal, Durban 4001, South Africa. Albericio@ukzn.ac.za falbericio@yachaytech.edu.ec albericio@irbbarcelona.org bgarcia@yachaytech.edu.ec.
authors: Prabhakar
authors: P
authors: Cherkupally
authors: Suhas
authors: S
authors: Ramesh
authors: Thavendran
authors: T
authors: Govender
authors: Hendrik G
authors: HG
authors: Kruger
authors: Beatriz G
authors: BG
authors: de la Torre
authors: Fernando
authors: F
authors: Albericio
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D002614:Chelating Agents / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D015195:Drug Design; D005227:Fatty Acids / Q000737:chemistry; D007501:Iron / Q000737:chemistry*; D015394:Molecular Structure; D008970:Molecular Weight; D009792:Oceans and Seas; D009842:Oligopeptides / Q000138:chemical synthesis*; D009930:Organic Chemicals; D009952:Ornithine / Q000737:chemistry; D010455:Peptides / Q000737:chemistry; D017262:Siderophores / Q000737:chemistry*; D014733:Vibrio / Q000378:metabolism; D014871:Water Microbiology
chemical_list: D000596:Amino Acids; D002614:Chelating Agents; D005227:Fatty Acids; D009842:Oligopeptides; D009930:Organic Chemicals; D010455:Peptides; D017262:Siderophores; C000599528:amphibactin-T; C000599529:moanachelin ala-B; D007501:Iron; D009952:Ornithine