Synthesis of biotinylated muramyl tripeptides with NOD2-stimulating activity

Bioorg Med Chem Lett. 2011 Jun 1;21(11):3362-6. doi: 10.1016/j.bmcl.2011.04.005. Epub 2011 Apr 9.

Abstract

Muramyl di- and tri-peptides are putative activators of the innate immune system through stimulation of the NOD2 receptor. To provide tools for the clarification of the mechanism of this activation we isolated different UDP-muramyl tripeptides (Lys- and DAP-type) from bacteria and used them to synthesize biotinylated derivatives. All biotinylated compounds retained their ability to activate NOD2 in a cell-based test system and are therefore suitable for binding studies aimed at identifying the appropriate pattern recognition receptor(s).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylmuramyl-Alanyl-Isoglutamine / analogs & derivatives*
  • Acetylmuramyl-Alanyl-Isoglutamine / chemical synthesis
  • Acetylmuramyl-Alanyl-Isoglutamine / chemistry
  • Acetylmuramyl-Alanyl-Isoglutamine / pharmacology
  • Adjuvants, Immunologic
  • Biotinylation
  • Gene Expression Regulation / drug effects
  • HEK293 Cells
  • Humans
  • Immunity, Innate*
  • Nod2 Signaling Adaptor Protein / metabolism*
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / chemistry
  • Oligopeptides / pharmacology

Substances

  • Adjuvants, Immunologic
  • Nod2 Signaling Adaptor Protein
  • Oligopeptides
  • Acetylmuramyl-Alanyl-Isoglutamine
  • muramylNAc-Ala-isoGln-Lys-tripeptide