(S)-4-5-dihydroxypentane-2-3-dione and 4-5-dihydroxy-2-3-pentanedione

Topics: Acyl-Butyrolactones; Animals; Anti-Bacterial Agents; Drug Discovery; Gram-Negative Bacteria; Gram-Positive Bacteria; Homoserine; Humans; Lactones; Molecular Structure; Pentanes; Peptides, Cyclic; Quorum Sensing; Structure-Activity Relationship

Ac2-DPD, the bis-(O)-acetylated derivative of 4,5-dihydroxy-2,3-pentanedione (DPD), was prepared both as a racemic mixture and in the optically active form found in naturally occurring DPD. It was shown to exhibit the same ability as DPD to induce bioluminescence in Vibrio harveyi and beta-galactosidase activity in Salmonella enterica Typhimurium, both gram-negative bacteria. Likewise, it was also shown to inhibit biofilm formation in gram-positive Bacillus cereus. The most likely hypothesis is that Ac2-DPD activity is due to the release of DPD by in situ hydrolysis of the ester groups. Importantly, by contrast with DPD, Ac2-DPD proved to be a stable compound which can be purified and stored.

Topics: Acetylation; Drug Stability; Homoserine; Hydrolysis; Lactones; Pentanes; Quorum Sensing; Stereoisomerism; Structure-Activity Relationship