134108-77-3Relevant articles and documents
Synthesis and stability of small molecule probes for Pseudomonas aeruginosa quorum sensing modulation
Glansdorp, Freija G.,Thomas, Gemma L.,Lee, Jungjoon K.,Dutton, Jenny M.,Salmond, George P. C.,Welch, Martin,Spring, David R.
, p. 3329 - 3336 (2007/10/03)
The human pathogen Pseudomonas aeruginosa uses N-butyryl-L-homoserine lactone (BHL) and N-(3-oxododecanyl)-L-homoserine lactone (OdDHL) as small molecule intercellular signals in a phenomenon known as quorum sensing (QS). QS modulators are effective at attenuating P. aeruginosa virulence; therefore, they are a potential new class of antibacterial agent. The lactone in BHL and OdDHL is hydrolysed under physiological conditions. The hydrolysis proceeds at a rate faster than racemisation of the α-chiral centre. Non-hydrolysable, non-racemic analogues (small molecule probes) were designed and synthesised, replacing the lactone with a ketone. OdDHL analogues were found to be relatively unstable to decomposition unless they were difluorinated between the β-keto amide. Stability studies on a non-hydrolysable, cyclohexanone analogue indicated that racemisation of the α-chiral centre was relatively slow. This analogue was assayed to show that the L-isomer is likely to be responsible for the QS autoinducing activity in P. aeruginosa and Serratia strain ATCC39006.
A General Method for the Separation of Enantiomeric trans-2-Substituted Cyclohexanols
Hoenig, Helmut,Seufer-Wasserthal, Peter
, p. 1137 - 1140 (2007/10/02)
An number of different racemic, trans-2-substituted cyclohexanols has been prepared in high optical purity by optical resolution of the respective 2'-substituted cyclohexyl butanoates with the aid of commercially available lipases.
