Synthesis and stereochemistry-activity relationship of small bacteriocin, an autoinducer of the symbiotic nitrogen-fixing bacterium Rhizobium leguminosarum

Organic Letters
Arata YajimaGoro Yabuta

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.

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Citations

Aug 9, 2011·Bioscience, Biotechnology, and Biochemistry·Arata Yajima
Feb 7, 2012·Journal of Molecular Biology·Justyna Aleksandra WojdylaColin Kleanthous
May 16, 2015·Natural Product Reports·Stefan Schulz, Susann Hötling
Sep 14, 2017·Chemical Society Reviews·D LeichnitzC Beemelmanns
Jan 1, 2010·Pharmacognosy Reviews·Mona SemaltyM S M Rawat
May 29, 2010·The Journal of Organic Chemistry·Rui FuPei-Qiang Huang

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