Abstract: Carbohydrates are the most abundant organic molecules on earth and are critical to a myriad of biological processes. The Vanderbilt Laboratory for Glycoscience uses a blend of synthetic organic chemistry and microbiology to elucidate the biological roles of carbohydrates, with a foci on advances in chemical synthesis and learning new mechanistic concepts. Our discussion will be divided into two categories: (1) the synthesis of structurally and biologically compelling complex carbohydrates, and (2) application of the host defense properties of human milk.