Synthesis of the peptaibol framework of the anticancer agent culicinin D: stereochemical assignment of the AHMOD moiety

Org Lett. 2012 Nov 16;14(22):5784-7. doi: 10.1021/ol302852q. Epub 2012 Nov 5.

Abstract

The postulated structure of the potent anticancer peptaibol culicinin D has been synthesized using Fmoc-based solid-phase peptide synthesis (SPPS). Comparison of the (1)H NMR data for the reported structure of culicinin D with the data obtained for the two synthetic polypeptides epimeric at C-6 in the AHMOD unit established the C-6 stereochemistry of the AHMOD residue in the natural product to be (R).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Ascomycota / chemistry
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / chemistry
  • Oligopeptides / pharmacology
  • Peptaibols / chemical synthesis*
  • Peptaibols / chemistry
  • Peptaibols / pharmacology
  • Peptides / chemical synthesis
  • Peptides / chemistry
  • Solid-Phase Synthesis Techniques

Substances

  • Antineoplastic Agents
  • Oligopeptides
  • Peptaibols
  • Peptides
  • culicinin D