Understanding the process of electron tunneling in chirality-induced singlemolecule junctions is imperative for the development of nanoscale switching and artificial nanomotors. Based on the combined non-equilibrium Greens functions formalism and the ground-state density functional theory, we present here the charge transport behavior of chiral gold (7,3) nanowires (NWs) in comparison with various other chiral and achiral 1D gold nanostructures as the principal leads to form stable single-molecule junctions. For σ-saturated alkane chains, we find that the contact potential barriers vary widely with the achiral leads but not with the chiral ones, although a close resemblance exists in the tunneling constants. Lower energy gaps for single-molecule junctions with Au(7,3)NWs ensure better electronic conductance even after allowing for the low thermal loss, due mainly to the close-packed arrangements of atoms with minimum wire tension. Our f irst − principles quantum transport analysis further suggests that chiral Au(7,3)NWs render higher electronic conductance than chiral gold (5,3) nanotubes (NTs), once bridged by either σ-saturated or π-conjugated molecular moieties. It, however, turns out that asymmetricity in the characteristics of channel formation at the lead-molecule contact remains often associated with chiral Au(7,3)NWs only.Recent years have seen a sizeable amount of study on one-dimensional (1D) nanostructures in the form of nanotubes (NTs) and nanowires (NWs), primarily because of their potential applications in nanodevice technology [1,2,3,4,5,6,7,8,9,10]. Among these, chiral nanostructures continue to garner interest due especially to their characteristic helicity that often displays the ability to control the physical properties in somewhat more flexible way. From conformational point of view, achiral nanostructures possess mirror planes while chiral nanostructures display no mirror symmetry but have glide planes. Magnetoelectronic properties are often found to be quite sensitive to chirality [1], apart from the band-related differences like band symmetry and band spacing between chiral and achiral carbon nanotubes (CNTs). Further, the impurity concentration and curvature effect turn out to be much stronger in chiral CNTs than in achiral ones[2].Although a major focus has remained for quite some time on developing CNT based field effect transistors (CNT-FETs) in a robust way, metallic nanotubes and nanowires have also received much attention [4,5,6,7,8,9] in the process.The underlying lattice for a gold nanotube is a 2D triangular network with one atom per unit cell, in contrast to a CNT that has a hexagonal framework.Another important difference is that gold nanotubes, unlike CNTs, always display metalicity due to its unique electronic nature. Using a tight-binding spiral model, Yevtushenko et al [9] have demonstrated that electronic transport may get affected considerably by the interplay between chirality and nonlinearity in a chiral CNT. However, the works by Manrique et al [10] reveal that like in...