Tetradecylamine

Deuterated methanol was purchased from Eurotop (Cambridge, UK). Mueller-Hinton Broth was purchased from Difco Laboratories (Detroit, MI, USA). Water from a Milli-Q Millipore system (Millipore, Burlington, MA, USA) was used to prepare aqueous solutions. Sodium myristate was from Sigma (San Luis, MO, USA). The N(π),N(τ)-bis(methyl)-L-Histidine tetradecyl amide (DMHNHC₁₄) was synthesized in our laboratory following a three-step procedure [15 (link)]: (a) Synthesis of N(α)-Cbz-N(π),N(τ)-bis(methyl)-L-Histidine using (CH₃)₂SO₄ (Sigma, San Luis, MO, USA) as a methylating agent, (b) preparation of the N(α)-Cbz-N(τ),N(π)-bis(methyl)-histidine tetradecyl amide simply heating the first intermediated with the tetradecyl amine (Sigma, San Luis, MO, USA) and (c) catalytic hydrogenation of intermediate 2 using Pd over charcoal (Sigma, San Luis, MO, USA). The detailed synthetic procedure as well as the characterization of DMHNHC₁₄ High-Performance Liquid Chromatography (HPLC), Mass spectrometry (MS) and (NMR) are provide elsewhere [15 (link)]. The N^α-lauroyl-N^εacetyl lysine (C₁₂C₃L) was obtained with a purity of 99% by the condensation of the dodecyl chloride (Sigma, San Luis, MO, USA) to the ε-amino group of the commercial acetyl-lysine. Its characterization is shown in the Supporting Information (Figures S9–S13).