Custom design of protein-dendron amphiphilic macromolecules is at the forefront of macromolecular engineering. Macromolecules having this architecture are very interesting because of their ability to self-assemble into various biomimetic nanoscopic structures. However, to date, there are no reports based on this concept due to the technical challenge associated with chemical synthesis. Towards that end, herein, we disclose a novel chemical methodology for the modular synthesis of a suite of monodisperse facially amphiphilic "protein-dendron" conjugates. Synthesis of functionalized monodisperse undeca(ethylene glycol) linker is obtained using a protection-deprotection strategy followed by coupling of hydrophobic benzyl-ether dendron of a various generation. The resultant conjugates are used for site-specific conjugation of globular protein to make monodisperse facially amphiphilic protein-dendron conjugates. These bio-hybrid conjugates have the ability to self-assemble into to supramolecular protein nanoassemblies. The self-assembly is primarily mediated by the strong hydrophobic interaction of benzyl-ether dendron domain. The size, surface charge, and oligomeric state of protein nanoassemblies could be systematically tuned by choosing an appropriate dendron or protein of interest. This chemical method discloses a new way to custom-make monodisperse facially amphiphilic protein-dendron bioconjugates.