Synthesis and stereochemistry-activity relationship of small bacteriocin, an autoinducer of the symbiotic nitrogen-fixing bacterium Rhizobium leguminosarum.
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.
Yajima
Arata
A
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
van Brussel
Anton A N
AA
Schripsema
Jan
J
Nukada
Tomoo
T
Yabuta
Goro
G
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
D001430:Bacteriocins; C088386:homoserine lactone; D009584:Nitrogen; D015107:4-Butyrolactone