Tethered bilayer lipid membranes can be used as model platforms to host membrane proteins or membrane-active peptides, which can act as transducers in sensing applications. Here we present the synthesis and characterization of a valinomycin derivative, a depsipeptide that has been functionalized to serve as a redox probe in a lipid bilayer. In addition, we discuss the influence of the molecular structure of the lipid bilayer on its ability to host proteins. By using electrical impedance techniques as well as neutron scattering experiments, a clear correlation between the packing density of the lipids forming the membrane and its ability to host membrane proteins could be shown.