N-Sulfonyl homoserine lactones as antagonists of bacterial quorum sensing
A series of 11 N-sulfonyl homoserine lactones has been synthesised. Some of them were found to competitively inhibit the action of 3-oxohexanoyl-L- homoserine lactone, the natural inducer of bioluminescence in the bacterium Vibrio fischeri. Molecular modeling suggests a possible explanation based on the prevention of structural rearrangements necessary for the formation of the active dimer of LuxR.
One-Step Synthesis of Esters of Aliphatic β-Chloro Sulfonic Acids. Their Sequential Conversion to Other Sulfonic Acid Derivatives
A one-step synthesis of methyl 2-chlorohexane-1- and 2-chlorooctane-1-sulfonate by the novel free-radical addition of methyl chlorosulfonate to 1-hexene and 1-octene, respectively, is reported.These products were converted by standard techniques into the corresponding sodium and benzylthiuronium β-chlorosulfonic acid salts and sulfonyl chlorides.Dehydrochlorination of these latter products with triethylamine affored regiospecific formation of trans-α,β-unsaturated sulfonyl chlorides, which were transformed by conventional methods into sodium and benzylthiuroniumunsaturated and saturated sulfonic acid salts.Eleven new compositions of matter are reported.
Heller, Morgan S.,Lorah, Dennis P.,Cox, Charles G.
p. 134 - 137
(2007/10/02)
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