title: 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.
abstract: 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.
authors.affiliation: Laboratoire de Chimie Organique, UMR 5181 CNRS, Université Lyon 1, INSA, Institut National des Sciences Appliquées, Bât. Jules Verne, 20 avenue A. Einstein, 69621 Villeurbanne, France.
authors.forename: Marine
authors.initials: M
authors.lastname: Frezza
authors.forename: Laurent
authors.initials: L
authors.lastname: Soulère
authors.forename: Damien
authors.initials: D
authors.lastname: Balestrino
authors.forename: Michel
authors.initials: M
authors.lastname: Gohar
authors.forename: Christian
authors.initials: C
authors.lastname: Deshayes
authors.forename: Yves
authors.initials: Y
authors.lastname: Queneau
authors.forename: Christiane
authors.initials: C
authors.lastname: Forestier
authors.forename: Alain
authors.initials: A
authors.lastname: Doutheau
mesh_terms: D000107:Acetylation; D004355:Drug Stability; D006714:Homoserine / Q000031:analogs & derivatives*; D006868:Hydrolysis; D007783:Lactones; D010420:Pentanes / Q000737:chemistry*; D053038:Quorum Sensing / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: C493138:4,5-dihydroxy-2,3-pentanedione; D007783:Lactones; C091088:N-octanoylhomoserine lactone; D010420:Pentanes; D006714:Homoserine