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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2017
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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 |
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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 |
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