Nanostructures were self-assembled in various media from the newly synthesized bolaamphiphiles, bis(N-alpha-amido-threonine)-1,3-propane dicarboxylate and the corresponding 1,7-heptane dicarboxylate. The self-assembly process was examined under varying pH conditions as well as in organic and mixed solvent systems. The nanostructures obtained were analyzed by various analytical methods. The range of sizes of the self-assembled structures were examined used dynamic light scattering. In particular, the nanotubular structures obtained were then functionalized with mucin, a highly glycosylated protein. The main goal of this work was to design mucoadhesive nanotubes and nanovesicles based on specific biological and physicochemical properties to achieve optimal mucoadhesion in the aqueous buccal environment. Since adhesion to the buccal surface is dependent on many conditions including hydrophilicity and charge, the bionanocomposites obtained after binding mucin to the nanostructures were examined. The samples were analyzed by AFM, TEM as well as via infrared spectroscopy. The nanotube to mucin ratio was also varied. It was found that the mucoadhesion was maximum when the ratio of mucin to nanotube was 2 to 1, after pre-hydration. Such biomaterials can be potentially useful as scaffolds for tissue engineering and for drug delivery.