Glycation Reactivity of a Quorum-Sensing Signaling Molecule

Angew Chem Int Ed Engl. 2016 Mar 14;55(12):4002-6. doi: 10.1002/anie.201511911. Epub 2016 Feb 17.

Abstract

Reported herein is that (4S)-4,5-dihydroxy-2,3-pentanedione (DPD) can undergo a previously undocumented non-enzymatic glycation reaction. Incubation of DPD with viral DNA or the antibiotic gramicidin S resulted in significant biochemical alterations. A protein-labeling method was consequently developed that facilitated the identification of unrecognized glycation targets of DPD in a prokaryotic system. These results open new avenues toward tracking and understanding the fate and function of the elusive quorum-sensing signaling molecule.

Keywords: fluorescent probes; glycation; protein modifications; proteomics; quorum sensing.

Publication types

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

MeSH terms

  • DNA / chemistry
  • Glucose / chemistry*
  • Pentanes / chemistry
  • Quorum Sensing*
  • Signal Transduction*

Substances

  • 4,5-dihydroxy-2,3-pentanedione
  • Pentanes
  • DNA
  • Glucose