Synthesis and isotopic labelling of N-acyl-L-homoserine lactone (AHL) derivatives – important quorum sensing autoinducers

Dorota Jakubczyk

Karlsruhe Institute of Technology (KIT), Kaiserstraße 12,
76131 Karlsruhe

email: dorota.jakubczyk@kit.edu

Natural biofilms are composed of complex communities of organisms, whose species composition responds highly dynamically to changing environmental conditions.

The research are focused on synthesis of the N-acyl-L-homoserine lactone (AHL) derivatives. AHL derivatives constitute an autoinducers that is produced by bacterial such as Pseudomonas aeruginosa and mediates cell-to-cell signalling.

We are interested in introducing functional groups to AHL molecules which can enable an immobilisation of these compounds to identify specific receptors in polymorphonuclear neutrophils (PMN).

In additional we need isotope labelled AHL (Figure 1) to detect the crossing of AHL through the membranes and its distribution with in the cell.

Moreover different synthetic strategies to get isotopic labelled AHL and functionalized AHL will be investigated.

Figure 1. a) DMAP, DCC; b) L-homoserine lactone, Et₃N [1].

[1] Chhabra, S. R., C. Harty, et al., Journal of Medicinal Chemistry, 2003, 46(1) 97-104.