Diketopiperazines as Cross-Communication Quorum- Sensing Signals between Cronobacter sakazakii and Bacillus cereus

Matheus R Bofinger; Lucas S de Sousa; José E N Fontes; Anita J Marsaioli

doi:10.1021/acsomega.6b00513

Diketopiperazines as Cross-Communication Quorum- Sensing Signals between Cronobacter sakazakii and Bacillus cereus

ACS Omega. 2017 Mar 31;2(3):1003-1008. doi: 10.1021/acsomega.6b00513. Epub 2017 Mar 16.

Authors

Matheus R Bofinger¹, Lucas S de Sousa¹, José E N Fontes¹, Anita J Marsaioli¹

Affiliation

¹ Institute of Chemistry, University of Campinas, P.O. Box 6154, 13084-971 Campinas, SP, Brazil.

Abstract

Herein, we reveal a second quorum-sensing system produced by Cronobacter sakazakii. A cyclo(l-Pro-l-Leu) diketopiperazine, detected in pure and mixed cultures of C. sakazakii and Bacillus cereus explains the coexistence of both in the same industrial environments. The molecule was identified by gas chromatography-mass spectrometry (GC-MS), ¹H, and ¹³C NMR, including 2D NMR (correlation spectroscopy, heteronuclear multiple bond correlation, and heteronuclear single quantum correlation), and the absolute configuration was compared with that of four synthetic standards produced by solid phase peptide synthesis using a chiral column on a GC-flame ionization detection. This article provides a new method to determine the absolute configuration of cyclo(Pro-Leu) diketopiperazine replacing the joint use of ¹H NMR and Marfey's method.