Resolution of the Confusion in the Assignments of Configuration for the Ciliatamides, Acylated Dipeptides from Marine Sponges

J Nat Prod. 2017 Oct 27;80(10):2845-2849. doi: 10.1021/acs.jnatprod.7b00684. Epub 2017 Oct 10.

Abstract

Direct comparison of authentic ciliatamide A with four synthetic isomers (1-4) by means of NMR and chiral-phase HPLC revealed that ciliatamide A possesses the 12R (d-N-MePhe residue) and 22S (l-Lys residue) configurations, which were not identical with either our previous assignment or those proposed by others through total synthesis. The absolute configuration of the methionine sulfoxide residue in ciliatamide D was also revised to be d.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chromatography, High Pressure Liquid
  • Dipeptides / chemistry*
  • Dipeptides / isolation & purification
  • Lipopeptides / chemistry*
  • Lipopeptides / isolation & purification
  • Marine Biology
  • Molecular Structure
  • Oxidation-Reduction
  • Porifera / chemistry*
  • Stereoisomerism

Substances

  • Dipeptides
  • Lipopeptides
  • ciliatamide A