An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing

Ascenso, Osvaldo S.; Marques, João C.; Santos, Ana Rita; Xavier, Karina B.; Ventura, M. Rita; Maycock, Christopher D.

doi:10.1016/j.bmc.2010.12.036

Cited by 42 publications

(64 citation statements)

References 23 publications

(16 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Gram-positive bacteria utilize oligopeptides as QS signals for the cell-to-cell communication (Li et al, 2012;Monnet and Gardan, 2015). Another signaling molecule known as autoinducer-2 (AI-2) that was derived from 4,5-dihydroxy-2,3-pentanedione (DPD) is deemed to be the omnipresent chemical as the interspecies communication signal between Gram-negative and Gram-positive bacteria (Ascenso et al, 2011;Galloway et al, 2010). …”

Section: Introductionmentioning

confidence: 99%

Characterization of N-acyl homoserine lactones (AHLs) producing bacteria isolated from vacuum-packaged refrigerated turbot (Scophthalmus maximus) and possible influence of exogenous AHLs on bacterial phenotype

Zhang

Zhu

Jatt

et al. 2016

J. Gen. Appl. Microbiol.

View full text Add to dashboard Cite

Quorum sensing (QS) is a cell-to-cell communication mechanism through which microbial cells communicate and regulate their wide variety of biological activities. N-acyl homoserine lactones (AHLs) are considered to be the most important QS signaling molecules produced by several Gramnegative bacteria. The present study aimed to screen the AHLs-producing bacteria from spoiled vacuum-packaged refrigerated turbot (Scophthalmus maximus) by biosensor assays, and the profiles of AHLs produced by these bacteria were determined using reversed-phase thin-layer chromatography (RP-TLC) and gas chromatography-mass spectrometry (GC-MS). Effects of exogenous AHLs and QS inhibitor (QSI) on the phenotypes (i.e., extracellular proteolytic activity and biofilm formation) of the AHLs-producing bacteria were also evaluated. Our results demonstrated that eight out of twenty-two isolates were found to produce AHLs. Three of the AHLs-producing isolates were identified as Serratia sp., and the other five were found to belong to the family of Aeromonas. Two isolates (i.e., S. liquefaciens A2 and A. sobria B1) with higher AHLs-producing activities were selected for further studies. Mainly, RP-TLC and GC-MS analysis revealed three AHLs, i.e., 3-oxo-C6-HSL, C8-HSL and C10-HSL were produced by S. liquefaciens A2, while five AHLs, i.e., C4-HSL, C6-HSL, C8-HSL, C10-HSL, and C12-HSL, were produced by A. sobria B1. Moreover, production of AHLs in both bacterial strains were found to be density-dependent, and the AHLs activity reached a maximum level in their middle logarithmic phase and decreased in the stationary phase. The addition of exogenous AHLs and QSI decreased the specific protease activity both of the Serratia A2 and Aeromonas B1. Exogenous AHLs inhibited the biofilm formation of Serratia A2 while it enhanced the biofilm formation in Aeromonas B1. QSI inhibited the specific protease activity and biofilm formation in both bacterial strains.

show abstract

Section: Introductionmentioning

confidence: 99%

Characterization of N-acyl homoserine lactones (AHLs) producing bacteria isolated from vacuum-packaged refrigerated turbot (Scophthalmus maximus) and possible influence of exogenous AHLs on bacterial phenotype

Zhang

Zhu

Jatt

et al. 2016

J. Gen. Appl. Microbiol.

View full text Add to dashboard Cite

show abstract

“…Compound R-6a [39] is known. NMR spectroscopic data for racemic compound 6a matched these reported for enantioenriched compound R-6a.…”

Section: -(2-chlorophenyl)-1-(trityloxy)but-3-yn-2-ol (5i)mentioning

confidence: 99%

Synthesis of Alkynyl‐Glycinols by Lewis Acid Catalyzed Propargylic Substitution of Bis‐Imidates

2015

View full text Add to dashboard Cite

Racemic and enantioenriched alkynyl‐glycinols can be synthesized by Lewis acid catalyzed cyclization reaction of bis‐trichloracetimidates derived from alkynyl‐glycols. The cyclization proceeds selectively to give 4‐alkynyl‐oxazolines as the propargylic substitution products. Enantioenriched bis‐imidates that contain an alkyl or trimethylsilyl substituent at the acetylene gave oxazolines with complete inversion of configuration. In turn, considerable racemization was observed in the cyclization of bis‐imidates that contain a phenyl substituent. The racemization for these substrates can be suppressed by introduction of the electronegative substituent at the phenyl ring. Oxazolines prepared by bis‐imidate cyclization reaction can be readily transformed to protected alkynyl‐glycol derivatives.

show abstract

“…DPD protected with a cyclohexylidene group was chemically synthesized by the recently developed method as reported in Ascenso et al (22) and dissolved in water to 10 mM. The cyclohexylidene-protecting group was removed with acidic Dowex 50WX8 resin (100 mg ml Ϫ1 of sample) also as reported previously (22).…”

Section: Dpd Synthesis and Preparationmentioning

confidence: 99%

“…The cyclohexylidene-protecting group was removed with acidic Dowex 50WX8 resin (100 mg ml Ϫ1 of sample) also as reported previously (22). Deprotected DPD was then neutralized with a final concentration of 30 mM potassium phosphate buffer, pH 7.2.…”

Section: Dpd Synthesis and Preparationmentioning

confidence: 99%

Processing the Interspecies Quorum-sensing Signal Autoinducer-2 (AI-2)

Marques

Lamosa

Russell

et al. 2011

Journal of Biological Chemistry

Self Cite

View full text Add to dashboard Cite

The molecule (S)-4,5-dihydroxy-2,3-pentanedione (DPD) is produced by many different species of bacteria and is the precursor of the signal molecule autoinducer-2 (AI-2). AI-2 mediates interspecies communication and facilitates regulation of bacterial behaviors such as biofilm formation and virulence. A variety of bacterial species have the ability to sequester and process the AI-2 present in their environment, thereby interfering with the cell-cell communication of other bacteria. This process involves the AI-2-regulated lsr operon, comprised of the Lsr transport system that facilitates uptake of the signal, a kinase that phosphorylates the signal to phospho-DPD (P-DPD), and enzymes (like LsrG) that are responsible for processing the phosphorylated signal. Because P-DPD is the intracellular inducer of the lsr operon, enzymes involved in P-DPD processing impact the levels of Lsr expression. Here we show that LsrG catalyzes isomerization of P-DPD into 3,4,4-trihydroxy-2-pentanone-5-phosphate. We present the crystal structure of LsrG, identify potential catalytic residues, and determine which of these residues affects P-DPD processing in vivo and in vitro. We also show that an lsrG deletion mutant accumulates at least 10 times more P-DPD than wild type cells. Consistent with this result, we find that the lsrG mutant has increased expression of the lsr operon and an altered profile of AI-2 accumulation and removal. Understanding of the biochemical mechanisms employed by bacteria to quench signaling of other species can be of great utility in the development of therapies to control bacterial behavior.Many bacteria regulate gene expression as a function of the density of the population. This process, called quorum sensing, enables these organisms to coordinate behaviors that are most beneficial when cells are working in unison (1, 2). Quorum sensing is mediated by signal molecules called autoinducers. One autoinducer (Autoinducer-2 (AI-2)3 ) is produced by many species of bacteria and can facilitate interspecies cell-cell signaling (3-5). AI-2 is produced by the enzyme LuxS, which synthesizes (S)-4,5-dihydroxy-2,3-pentanedione (DPD; Fig. 1A, 1), the linear form of a set of interconverting molecules with AI-2 activity (6 -8). AI-2 (or its synthase LuxS) has been shown to regulate important bacterial behaviors such as biofilm formation and the production of virulence factors (4, 5, 9, 10). Thus, one strategy for controlling these behaviors is to control the concentration (or availability) of AI-2. We have previously shown that certain bacteria can employ this strategy by processing AI-2 and thus quenching interspecies signaling (11). These bacteria include most members from the Enterobacteriaceae family (like the commensal Escherichia coli K12 and the pathogens E. coli O157 and Salmonella typhimurium) but also more distantly related bacteria such as the plant symbiont Sinorhizobium meliloti and the pathogen Bacillus anthracis (12).In these bacteria, AI-2 controls the expression of a system (named Lsr for luxS-regulated)...

show abstract

An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing

Cited by 42 publications

References 23 publications

Characterization of <i>N</i>-acyl homoserine lactones (AHLs) producing bacteria isolated from vacuum-packaged refrigerated turbot (<i>Scophthalmus maximus</i>) and possible influence of exogenous AHLs on bacterial phenotype

Characterization of <i>N</i>-acyl homoserine lactones (AHLs) producing bacteria isolated from vacuum-packaged refrigerated turbot (<i>Scophthalmus maximus</i>) and possible influence of exogenous AHLs on bacterial phenotype

Synthesis of Alkynyl‐Glycinols by Lewis Acid Catalyzed Propargylic Substitution of Bis‐Imidates

Processing the Interspecies Quorum-sensing Signal Autoinducer-2 (AI-2)

Contact Info

Product

Resources

About