Studies Toward the Chemical Synthesis of Lacto-N-neotetraose

Abstract

Human milk oligosaccharides (HMOs) are a diverse class of carbohydrates that are unique to human milk. These oligosaccharides have been demonstrated to influence infant health through several mechanisms including helping to establish a healthy gut microbiome and deterring pathogenic infection. To understand the manner through which HMOs impart these benefits, it is important to conduct studies using single-entity compounds. The difficulty in isolating pure oligosaccharides from breastmilk has created a demand to access these carbohydrates synthetically. This work aimed to synthesize the human milk tetrasaccharide lacto-N-neotetraose. In the synthesis, an orthogonal protecting group strategy was employed to facilitate access to human milk pentasaccharides.