title: Synthesis and stereochemistry-activity relationship of small bacteriocin, an autoinducer of the symbiotic nitrogen-fixing bacterium Rhizobium leguminosarum.
abstract: The four stereoisomers of small bacteriocin, an autoinducer of the symbiotic nitrogen-fixing bacterium Rhizobium leguminosarum, were synthesized via a versatile methodology for 3'-hydroxyacyl homoserine lactones based on the Nagao asymmetric aldol reaction. The synthetic isomers were much less effective at inhibiting the growth of R. leguminosarum RBL5523 than the natural isomer, showing the importance of stereochemistry for activity.
authors.affiliation: Department of Fermentation Science, Faculty of Applied Biological Science, Tokyo University of Agriculture NODAI, Sakuragaoka 1-1-1, Setagaya-ku, Tokyo 156-8502, Japan. ayaji@nodai.ac.jp
authors.forename: Arata
authors.initials: A
authors.lastname: Yajima
authors.forename: Anton A N
authors.initials: AA
authors.lastname: van Brussel
authors.forename: Jan
authors.initials: J
authors.lastname: Schripsema
authors.forename: Tomoo
authors.initials: T
authors.lastname: Nukada
authors.forename: Goro
authors.initials: G
authors.lastname: Yabuta
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001430:Bacteriocins / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D016961:Rhizobium leguminosarum / Q000737:chemistry* / Q000187:drug effects; D013237:Stereoisomerism
chemical_list: D001430:Bacteriocins; C088386:homoserine lactone; D009584:Nitrogen; D015107:4-Butyrolactone