Cargando…

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

[Image: see text] 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...

Descripción completa

Detalles Bibliográficos
Autores principales: Bofinger, Matheus R., de Sousa, Lucas S., Fontes, José E. N., Marsaioli, Anita J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6044783/
https://www.ncbi.nlm.nih.gov/pubmed/30023625
http://dx.doi.org/10.1021/acsomega.6b00513
_version_ 1783339541226061824
author Bofinger, Matheus R.
de Sousa, Lucas S.
Fontes, José E. N.
Marsaioli, Anita J.
author_facet Bofinger, Matheus R.
de Sousa, Lucas S.
Fontes, José E. N.
Marsaioli, Anita J.
author_sort Bofinger, Matheus R.
collection PubMed
description [Image: see text] 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), (1)H, and (13)C 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 (1)H NMR and Marfey’s method.
format Online
Article
Text
id pubmed-6044783
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-60447832018-07-16 Diketopiperazines as Cross-Communication Quorum-Sensing Signals between Cronobacter sakazakii and Bacillus cereus Bofinger, Matheus R. de Sousa, Lucas S. Fontes, José E. N. Marsaioli, Anita J. ACS Omega [Image: see text] 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), (1)H, and (13)C 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 (1)H NMR and Marfey’s method. American Chemical Society 2017-03-16 /pmc/articles/PMC6044783/ /pubmed/30023625 http://dx.doi.org/10.1021/acsomega.6b00513 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Bofinger, Matheus R.
de Sousa, Lucas S.
Fontes, José E. N.
Marsaioli, Anita J.
Diketopiperazines as Cross-Communication Quorum-Sensing Signals between Cronobacter sakazakii and Bacillus cereus
title Diketopiperazines as Cross-Communication Quorum-Sensing Signals between Cronobacter sakazakii and Bacillus cereus
title_full Diketopiperazines as Cross-Communication Quorum-Sensing Signals between Cronobacter sakazakii and Bacillus cereus
title_fullStr Diketopiperazines as Cross-Communication Quorum-Sensing Signals between Cronobacter sakazakii and Bacillus cereus
title_full_unstemmed Diketopiperazines as Cross-Communication Quorum-Sensing Signals between Cronobacter sakazakii and Bacillus cereus
title_short Diketopiperazines as Cross-Communication Quorum-Sensing Signals between Cronobacter sakazakii and Bacillus cereus
title_sort diketopiperazines as cross-communication quorum-sensing signals between cronobacter sakazakii and bacillus cereus
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6044783/
https://www.ncbi.nlm.nih.gov/pubmed/30023625
http://dx.doi.org/10.1021/acsomega.6b00513
work_keys_str_mv AT bofingermatheusr diketopiperazinesascrosscommunicationquorumsensingsignalsbetweencronobactersakazakiiandbacilluscereus
AT desousalucass diketopiperazinesascrosscommunicationquorumsensingsignalsbetweencronobactersakazakiiandbacilluscereus
AT fontesjoseen diketopiperazinesascrosscommunicationquorumsensingsignalsbetweencronobactersakazakiiandbacilluscereus
AT marsaiolianitaj diketopiperazinesascrosscommunicationquorumsensingsignalsbetweencronobactersakazakiiandbacilluscereus