This dissertation presents a simple but effective method for the design and synthesis of molecularly imprinted nanoparticles (MINPs) as antibody mimics. The MINPs resembled proteins in their water-solubility, discrete nanosized structure, and in their ability to contain hydrophobic binding pockets in the interior while maintaining a hydrophilic exterior by virtue of the sugar-derived ligands incorporated onto the surface during the post-functionalization. A variety of MINPs with guest-tailored and modifiable hydrophobic binding pockets were synthesized and their applications in biomimetic recognition, molecular sensing, and generation of plastic monoclonal antibodies investigated.