New polymers with exceptional properties are needed for applications in high-performance structures, novel electrical, optical and electro-optical devices, and for multi-functional smart materials. Concurrently, new computational capabilities and methods for properties prediction and analysis have enabled the study of a variety of polymer chain architectures to examine the principles that govern their high-performance properties. By semi-empirical and ab initio computational methods, flexible, stiff-chain, rigid-rod, and biological structures could be analyzed. Single chain molecular stress-strain curves for axial tension and compression were calculated, and the strain dependence of the molecular modulus and vibrational frequencies were compared to measurements of molecular deformation, such as IR and Raman spectroscopy. However, of special interest is the distinctly different response of alpha-helical biopolymer chains to strain. Indeed, in this study we compare on a theoretical basis the ‘spring-like’ microscopic mechanical response of alpha-helical biopolymers having a reinforcing intra-molecular hydrogen bonding network to analogous synthetic extended chain polymers, especially poly(para-phenylene terephthalamide) (PPTA) [KEVLARTM]. The theoretical verification of the absence of compressive buckling in alpha-helical biopolymer chains rationalizes the molecular elasticity and resistance to ‘kinking’ of those strands, manifested by the prevalence in Nature for coiled coils. The understanding of the structure-tofunction relationship in biopolymers explaining the role of the alpha-helix in these systems as a requirement for superior compressive mechanical properties, may enable new guidance for the synthesis of motifs consistent with molecular frameworks optimized by Nature.