Medusamide A, a Panamanian Cyanobacterial Depsipeptide with Multiple β-Amino Acids

Org Lett. 2016 Feb 5;18(3):352-5. doi: 10.1021/acs.orglett.5b03110. Epub 2016 Jan 19.

Abstract

From a collection of marine cyanobacteria made in the Coiba National Park along the Pacific coast of the Republic of Panama a novel cyclic depsipeptide, given the trivial name medusamide A, has been isolated and fully characterized. Medusamide A contains four contiguous β-amino acid (2R,3R)-3-amino-2-methylhexanoic acid (Amha) residues. This is the first report of multiple Amha residues and contiguous β-amino acid residues within a single cyclic peptide-type natural product. Stereochemical assignment of the Amha residues was completed following the synthesis of reference standards for this β-amino acid and the subsequent derivatization with Marfey's reagent and LC-MS analysis.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aminocaproates / chemistry
  • Cyanobacteria / chemistry*
  • Depsipeptides / chemistry
  • Depsipeptides / isolation & purification*
  • Depsipeptides / pharmacology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Panama
  • Stereoisomerism

Substances

  • Aminocaproates
  • Depsipeptides
  • medusamide A
  • 2-amino-5-methyl-5-hexenoic acid