This book discusses the influence of chirality and intermolecular interactions in biomimetic (amphiphilic and peptide systems) and biological (amino acids and model biological reactions involving amino acids and peptides) systems using computational chemical methods. Generation and retention of homochirality are fundamentally important in biology. The difference in intermolecular interactions between enantiomeric and racemic pairs (homochiral and heterochiral interactions) and their interactions with the surrounding molecular structures leading to chiral discrimination, which could be responsible for homochiral preference, is also discussed. The nature of intermolecular energy surfaces as a function of molecular mutual orientations dictates the chiral discrimination in biology. The knowledge gained in the biomimetic systems is employed to understand more complex biological reactions like synthesis of amino acids by transamination reaction, synthesis of aminoacyl-tRNA in the aminoacylation process and synthesis of peptides in ribosome. The molecular recognition process in biomimetic amphiphiles and peptides are correlated with the nature of the intermolecular energy surfaces.