Ac2-DPD, the bis-(O)-acetylated derivative of 4,5-dihydroxy-2,3-pentanedione (DPD) is a convenient stable precursor of bacterial quorum sensing autoinducer AI-2.

Marine Frezza (1) , Laurent Soulère (1) , Damien Balestrino (2) , Michel Gohar , Christian Deshayes (3) , Yves Queneau (4) , Christiane Forestier (2) , Alain Doutheau (1)

1 ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
2 LMGE - Laboratoire Microorganismes : Génome et Environnement
3 MGM - Microbiologie et Génétique Moléculaire
4 COB - Chimie Organique et Bioorganique

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.

Mots clés: Acetylation; Drug Stability; Homoserine; Hydrolysis; Lactones; Quorum Sensing; Stereoisomerism; Structure-Activity Relationship

Mots clés: Pentanes

Domaines: Biologie moléculaire

Marine Frezza, Laurent Soulère, Damien Balestrino, Michel Gohar, Christian Deshayes, et al.. Ac2-DPD, the bis-(O)-acetylated derivative of 4,5-dihydroxy-2,3-pentanedione (DPD) is a convenient stable precursor of bacterial quorum sensing autoinducer AI-2.. Bioorganic and Medicinal Chemistry Letters, 2007, 17 (5), pp.1428-31. ⟨10.1016/j.bmcl.2006.11.076⟩. ⟨hal-00164190⟩