N-Acylated amino acid methyl esters from marine Roseobacter group bacteria

• Hilke Bruns,
• Lisa Ziesche,
• Nargis Khakin Taniwal,
• Laura Wolter,
• Thorsten Brinkhoff,
• Jennifer Herrmann,
• Rolf Müller and
• Stefan Schulz

Beilstein J. Org. Chem. 2018, 14, 2964–2973, doi:10.3762/bjoc.14.276

• derivatives; 2-aminobutyric acid; homoserine lactones; natural products; quorum sensing; Introduction The identification and structural elucidation of naturally occurring compounds traditionally requires isolation and NMR investigation as key method to detect novel compounds and new structural classes

Non-native autoinducer analogs capable of modulating the SdiA quorum sensing receptor in Salmonella enterica serovar Typhimurium

• Matthew J. Styles and
• Helen E. Blackwell

Beilstein J. Org. Chem. 2018, 14, 2651–2664, doi:10.3762/bjoc.14.243

• sub-libraries consisted of substituted phenylacetanoyl homoserine lactones (PHLs), phenylpropionyl homoserine lactones (PPHLs), and phenoxyacetyl homoserine lactones (POHLs), many of which we have previously found to be highly active in a range of LuxR-type receptors as both agonists and competitive

• antagonists [45][47][48][51][56]. The Q and R sub-libraries contain a related group of substituted benzoyl homoserine lactones (BHLs) [56]. Sub-library S probed the effects of branched alkyl groups on the acyl tail [56]. The F sub-library contained a variety of AHL analogs with alternative, often hydrolysis

Targeting the Pseudomonas quinolone signal quorum sensing system for the discovery of novel anti-infective pathoblockers

• Christian Schütz and
• Martin Empting

Beilstein J. Org. Chem. 2018, 14, 2627–2645, doi:10.3762/bjoc.14.241

• actually autoinducers (AIs) and, hence, have an agonistic activity toward their receptor, a positive feedback loop is created. In P. aeruginosa three different chemotypes of AIs have been identified, to date: alkyl homoserine lactones (AHLs) used by the las and rhl systems, alkylquinolones (AQs) used by

Posttranslational isoprenylation of tryptophan in bacteria

• Masahiro Okada,
• Tomotoshi Sugita and
• Ikuro Abe

Beilstein J. Org. Chem. 2017, 13, 338–346, doi:10.3762/bjoc.13.37

• in boldface and colored blue. (B) Chemical structures of acyl homoserine lactones. The acyl side chains are shown in boldface. (A) Schematic representation of the signal transduction cascade of quorum sensing stimulated by the ComX pheromone in B. subtilis. (B) Amino acid sequences of the aspartate

Discovery of an inhibitor of the production of the Pseudomonas aeruginosa virulence factor pyocyanin in wild-type cells

• Bernardas Morkunas,
• Balint Gal,
• Warren R. J. D. Galloway,
• James T. Hodgkinson,
• Brett M. Ibbeson,
• Yaw Sing Tan,
• Martin Welch and
• David R. Spring

Beilstein J. Org. Chem. 2016, 12, 1428–1433, doi:10.3762/bjoc.12.137

• types of quorum sensing systems. Two of the QS signaling systems in P. aeruginosa utilise N-acylated-L-homoserine lactones (AHLs) as signalling molecules [20][21][22]. The rhl system utilises N-butanoyl-L-homoserine lactone (BHL) and it’s cognate receptor RhlR [20][21][22]. The las system utilises N-(3

Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators

• Michail Syrpas,
• Ewout Ruysbergh,
• Christian V. Stevens,
• Norbert De Kimpe and
• Sven Mangelinckx

Beilstein J. Org. Chem. 2014, 10, 2539–2549, doi:10.3762/bjoc.10.265

• Michail Syrpas Ewout Ruysbergh Christian V. Stevens Norbert De Kimpe Sven Mangelinckx Department of Sustainable Organic Chemistry and Technology, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium 10.3762/bjoc.10.265 Abstract Novel N-α-haloacylated homoserine lactones, in which a halogen

• atom was introduced at the α-position of the carbonyl function of the N-acyl chain, have been studied as quorum sensing (QS) modulators and compared with a library of natural N-acylated homoserine lactones (AHLs). The series of novel analogues consists of α-chloro, α-bromo and α-iodo AHL analogues

• . Most of the α-haloacylated analogues did not exhibit a significant reduction when tested in the QS inhibition test. Therefore, these novel analogues could be utilized as chemical probes for QS structure–activity studies. Keywords: halogenated fatty acids; halogenation; N-acylated homoserine lactones