Synthesis of Deuterated Aminocaproyl Linkers

Abstract

Gramicidin A (gA) analogues with a biotin attached to the C-terminus by an aminocaproyl linker are used as ion channels in the AMBRI® biosensor and are referred to as biotinylated gA. In order to examine the conformation and dynamics of the aminocaproyl linker by ²H solid-state nuclear magnetic resonance, the synthesis of deuterated aminocaproic acid is required. We report on the synthesis of (D₁₀)-6-aminocaproic acid from commercially available perdeuterated cyclohexanol and its covalent attachment to the C-terminal group of gA to form gAX_DXB.