title: Deuterium-labelled N-acyl-L-homoserine lactones (AHLs)--inter-kingdom signalling molecules--synthesis, structural studies, and interactions with model lipid membranes.
abstract: N-Acyl-L-homoserine lactones (AHLs) are synthesized by Gram-negative bacteria. These quorum-sensing molecules play an important role in the context of bacterial infection and biofilm formation. They also allow communication between microorganisms and eukaryotic cells (inter-kingdom signalling). However, very little is known about the entire mechanism of those interactions. Precise structural studies are required to analyse the different AHL isomers as only one form is biologically most active. Theoretical studies combined with experimental infrared and Raman spectroscopic data are therefore undertaken to characterise the obtained compounds. To mimic interactions between AHL and cell membranes, we studied the insertion of AHL in supported lipid bilayers, using vibrational sum-frequency-generation spectroscopy. Deuterium-labelled AHLs were thus synthesized. Starting from readily available deuterated fatty acids, a two-step procedure towards deuterated N-acyl-L-homoserine lactones with varying chain lengths is described. This included the acylation of Meldrum's acid followed by amidation. Additionally, the detailed analytical evaluation of the products is presented herein.
authors.affiliation: Karlsruhe Institute of Technology, Institute of Organic Chemistry, Karlsruhe, Germany.
authors.forename: Dorota
authors.initials: D
authors.lastname: Jakubczyk
authors.forename: Christoph
authors.initials: C
authors.lastname: Barth
authors.forename: Adam
authors.initials: A
authors.lastname: Kubas
authors.forename: Frances
authors.initials: F
authors.lastname: Anastassacos
authors.forename: Patrick
authors.initials: P
authors.lastname: Koelsch
authors.forename: Karin
authors.initials: K
authors.lastname: Fink
authors.forename: Ute
authors.initials: U
authors.lastname: Schepers
authors.forename: Gerald
authors.initials: G
authors.lastname: Brenner-Weiß
authors.forename: Stefan
authors.initials: S
authors.lastname: Bräse
mesh_terms: D054742:Acyl-Butyrolactones / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D003903:Deuterium / Q000737:chemistry; D006090:Gram-Negative Bacteria / Q000737:chemistry / Q000378:metabolism*; D008563:Membrane Lipids / Q000378:metabolism*; D008958:Models, Molecular; D015394:Molecular Structure; D015398:Signal Transduction
chemical_list: D054742:Acyl-Butyrolactones; D008563:Membrane Lipids; D003903:Deuterium