Bio-inspired supramolecular chemistry harnesses the principles of non-covalent interactions, particularly hydrogen bonding, to design novel molecular assemblies with enhanced structural and functional properties. This study employs quantum-chemical approaches based on Kohn-Sham density functional theory (KS-DFT) to elucidate the nature of hydrogen bonding in both biological and synthetic supramolecular systems. By analyzing hydrogen-bonded base pairs, DNA duplex stability, guanine-quadruplex structures, and hydrogen-bonded amides, we establish how electronic interactions govern molecular stability and reactivity. Our findings demonstrate that the charge transfer component of hydrogen bonding, rather than electrostatics alone, plays a critical role in dictating molecular behavior. The results provide theoretical insights for the rational design of novel materials, biomimetic structures, and potential applications in catalysis and molecular electronics.