Assignment of the Absolute Configuration of Phosphoeleganin via Synthesis of Model Compounds

J Nat Prod. 2017 Jul 28;80(7):2118-2123. doi: 10.1021/acs.jnatprod.7b00397. Epub 2017 Jul 12.

Abstract

The full absolute configuration assignment of phosphoeleganin (1), a recently discovered marine-derived phosphorylated polyketide with protein tyrosine phosphatase 1B inhibitory activity, was achieved. It was based on the synthesis of model diasteroisomeric compounds of the C-8-C-12 segment portion of phosphoeleganin, chiral derivatization methods, and application of the universal NMR database concept.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Databases, Factual
  • Marine Biology
  • Models, Chemical
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Polyketides / chemical synthesis
  • Polyketides / chemistry*
  • Polyketides / pharmacology
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
  • Stereoisomerism

Substances

  • Polyketides
  • phosphoeleganin
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1