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Angewandte Chemie
Vol. 55 (12), 2016, Pages: 4002–4006

Glycation Reactivity of a Quorum-Sensing Signaling Molecule

Dr. Kyoji Tsuchikama, Dr. Major Gooyit, Dr. Tyler L. Harris, Dr. Jie Zhu, Dr. Daniel Globisch, Dr. Gunnar F. Kaufmann, Dr. Kim D. Janda

The Skaggs Institute for Chemical Biology and Departments of Chemistry, Immunology and Microbial Science, The Scripps Research Institute, La Jolla, CA, USA.


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.


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