Structure Revision of Similanamide to PF1171C by Total Synthesis

J Nat Prod. 2015 Sep 25;78(9):2286-91. doi: 10.1021/acs.jnatprod.5b00643. Epub 2015 Sep 8.

Abstract

The total synthesis of the proposed structure of similanamide, a cyclic hexapeptide recently isolated from the marine sponge-associated fungus Aspergillus similanensis KUFA 0013, was achieved by solid-phase synthesis of a linear precursor and solution-phase macrolactamization. The NMR spectra of our synthetic final product were not identical to those of the isolated material and led us to conclude that similanamide is identical to PF1171C, a previously reported diastereomeric hexapeptide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Marine Biology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides, Cyclic / chemistry*
  • Porifera / chemistry*
  • Solid-Phase Synthesis Techniques

Substances

  • PF1171C
  • Peptides, Cyclic