Journal
ORGANIC LETTERS
Volume 10, Issue 10, Pages 2047-2050Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol8005198
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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.
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