title: An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing.
abstract: Autoinducer-2 (AI-2) is a signalling molecule for bacterial inter-species communication. A synthesis of (S)-4,5-dihydroxypentane-2,3-dione (DPD), the precursor of AI-2, is described starting from methyl glycolate. The key step was an asymmetric reduction of a ketone with (S)-Alpine borane. This new method was highly reproducible affording DPD for biological tests without contaminants. The biological activity was tested with the previously available assays and compared with a new method using an Escherichia coli reporter strain thus avoiding the use of the pathogenic Salmonella reporter.
authors.affiliation: Instituto de Tecnologia Química e Biológica, Universidade Nova de Lisboa, Apartado 127, 2780-901 Oeiras, Portugal.
authors.forename: Osvaldo S
authors.initials: OS
authors.lastname: Ascenso
authors.forename: João C
authors.initials: JC
authors.lastname: Marques
authors.forename: Ana Rita
authors.initials: AR
authors.lastname: Santos
authors.forename: Karina B
authors.initials: KB
authors.lastname: Xavier
authors.forename: M Rita
authors.initials: MR
authors.lastname: Ventura
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Maycock
mesh_terms: D004340:Drug Contamination; D004926:Escherichia coli / Q000235:genetics / Q000502:physiology*; D006714:Homoserine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D007783:Lactones / Q000737:chemistry* / Q000378:metabolism*; D010422:Pentanones / Q000138:chemical synthesis* / Q000378:metabolism; D053038:Quorum Sensing; D015203:Reproducibility of Results
chemical_list: C551402:4,5-dihydroxypentane-2,3-dione; D007783:Lactones; C091088:N-octanoylhomoserine lactone; D010422:Pentanones; D006714:Homoserine