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

Org Biomol Chem. 2015 Apr 28;13(16):4760-8. doi: 10.1039/c5ob00100e.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry
  • Chelating Agents / chemistry
  • 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
  • Siderophores / chemistry*
  • Vibrio / metabolism
  • Water Microbiology

Substances

  • Amino Acids
  • Chelating Agents
  • Fatty Acids
  • Oligopeptides
  • Organic Chemicals
  • Peptides
  • Siderophores
  • amphibactin-T
  • moanachelin ala-B
  • Iron
  • Ornithine