106983-26-0Relevant articles and documents
Acyl-homoserine lactones from Erwinia psidii R. IBSBF 435T, a guava phytopathogen (Psidium guajava L.)
Pomini, Armando M.,Manfio, Gilson P.,Araujo, Welington L.,Marsaioli, Anita J.
, p. 6262 - 6265 (2005)
The phytopathogen Erwinia psidii R. IBSBF 435T causes rot in branches, flowers, and fruits of guava (Psidium guajava L.), being responsible for crop losses, and has no effective control. It was demonstrated that this strain produces two compounds [S-(-)-N-hexanoyl and N-heptanoyl-homoserine lactone], both belonging to the class of quorum-sensing signaling substances. A protocol using gas chromatography - flame ionization detection with chiral stationary phase is described for the absolute configuration determination of a natural acyl-homoserine lactone. Biological assays with specific reporter and synthesis of identified substances are also described. This is the first report on the N-heptanoyl-homoserine lactone occurrence in the Erwinia genus.
Deuterium and tritium labelling of N-acyl-L-homoserine lactones (AHLs) by catalytic reduction of a double bond in the layer-by-layer method
Jakubczyk, Dorota,Merle, Christian,Brenner-Weiss, Gerald,Luy, Burkhard,Braese, Stefan
, p. 5323 - 5330 (2013)
N-Acyl-L-homoserine lactones (AHLs) are signalling molecules found in Gram-negative bacteria that enable bacteria to communicate with each other through quorum sensing and with their eukaryotic host cells through inter-kingdom signalling. Very little is known about inter-kingdom signalling mechanisms. Deuterium- and tritium-labelled AHLs were synthesized in an effort to detect the cellular distribution and monitor the membrane transport of AHLs. Most tritium labelling methods use tritium gas, which is difficult to handle, however, here we present a novel, gas-free method with which to obtain deuterium- and tritium-label terminally unsaturated AHLs through catalytic reduction of the double bond. This uncommon double bond reduction employs either sodium borohydride-[2H] or sodium borohydride-[3H] and is performed in the presence of palladium(II) acetate, which acts as a catalyst in the unique layer-by-layer system. Moreover, detailed NMR analysis of the resulting isotopologues is presented. A novel, gas-free method of deuterium- and tritium-labelling of terminally unsaturated AHLs is described. The catalytic reduction of the double bond by sodium borohydrides is performed in the presence of palladium(II) acetate, which acts as a catalyst in the unique layer-by-layer system. Copyright
Absolute configuration and antimicrobial activity of acylhomoserine lactones
Pomini, Armando M.,Marsaioli, Anita J.
experimental part, p. 1032 - 1036 (2009/04/06)
(S)-N-Heptanoylhomoserine lactone is an uncommon acyl odd-chain natural product employed by many Gram-negative bacteria as a signaling substance in chemical communication mechanisms known as quorum sensing. The absolute configuration determination of the metabolite produced by the phytopathogen Pantoea ananatis Serrano is reported herein. As with all other substances of this class, the lactone moiety possesses S configuration, corroborating the hypothesis that it shares the same biosynthetic pathway as the (S)-N-hexanoylhomoserine lactone and also that some LuxI homologues can accept both hexanoyl- and heptanoyl-ACP as precursors. Evaluation of the antimicrobial activity of enantiomeric acylhomoserine lactones against three Gram-positive bacteria (Bacillus cereus, B. subtilis, and Staphylococcus aureus) revealed important features between absolute configuration and antimicrobial activity. The N-heptanoylhomoserine lactone was considerably less active than the 3-oxo derivatives. Surprisingly, non-natural (R)-N-(3-oxo-octanoyl)homoserine lactone was as active as the S enantiomer against B. cereus, while the synthetic racemic product was less active than either enantiomer.
