Peptidoglycan Metabolite Photoaffinity Reporters Reveal Direct Binding to Intracellular Pattern Recognition Receptors and Arf GTPases

ACS Chem Biol. 2019 Mar 15;14(3):405-414. doi: 10.1021/acschembio.8b01038. Epub 2019 Feb 20.

Abstract

The peptidoglycan fragments γ-d-glutamyl- meso-diaminopimelic acid (iE-DAP) and muramyl-dipeptide (MDP) are microbial-specific metabolites that activate intracellular pattern recognition receptors and stimulate immune signaling pathways. While extensive structure-activity studies have demonstrated that these bacterial cell wall metabolites trigger NOD1- and NOD2-dependent signaling, their direct binding to these innate immune receptors or other proteins in mammalian cells has not been established. To characterize these fundamental microbial metabolite-host interactions, we synthesized a series of peptidoglycan metabolite photoaffinity reporters and evaluated their cross-linking to NOD1 and NOD2 in mammalian cells. We show that active iE-DAP and MDP photoaffinity reporters selectively cross-linked NOD1 and NOD2, respectively, and not their inactive mutants. We also discovered MDP reporter cross-linking to Arf GTPases, which interacted most prominently with GTP-bound Arf6 and coimmunoprecipitated with NOD2 upon MDP stimulation. Notably, MDP binding to NOD2 and Arf6 was abrogated with loss-of-function NOD2 mutants associated with Crohn's disease. Our studies demonstrate peptidoglycan metabolite photoaffinity reporters can capture their cognate immune receptors in cells and reveal unpredicted ligand-induced interactions with other cellular cofactors. These photoaffinity reporters should afford useful tools to discover and characterize other peptidoglycan metabolite-interacting proteins.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • ADP-Ribosylation Factors / metabolism*
  • Acetylmuramyl-Alanyl-Isoglutamine / metabolism*
  • Cell Wall / metabolism
  • Cytokines / metabolism
  • Diaminopimelic Acid / analogs & derivatives*
  • Diaminopimelic Acid / metabolism
  • HEK293 Cells
  • Humans
  • Ligands
  • Mutant Proteins / metabolism
  • Mutation
  • Nod1 Signaling Adaptor Protein / metabolism
  • Nod2 Signaling Adaptor Protein / metabolism
  • Peptidoglycan / metabolism*
  • Protein Binding
  • Receptors, Pattern Recognition / metabolism*
  • Signal Transduction
  • Structure-Activity Relationship

Substances

  • Cytokines
  • Ligands
  • Mutant Proteins
  • Nod1 Signaling Adaptor Protein
  • Nod2 Signaling Adaptor Protein
  • Peptidoglycan
  • Receptors, Pattern Recognition
  • Acetylmuramyl-Alanyl-Isoglutamine
  • Diaminopimelic Acid
  • N(2)-(gamma-D-glutamyl)-meso-2,2'-diaminopimelic acid
  • ADP-Ribosylation Factors