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Title page for ETD etd-07202016-172138

Type of Document Master's Thesis
Author Hayes, John Philip
URN etd-07202016-172138
Title Studies Toward the Chemical Synthesis of Lacto-N-neotetraose
Degree Master of Science
Department Chemistry
Advisory Committee
Advisor Name Title
Steven Townsend Committee Chair
Gary Sulikowski Committee Member
  • human milk oligosaccharide
  • HMO
  • carbohydrate synthesis
  • carbohydrates
  • lacto-n-neotetraose
  • LNnT
  • human milk tetrasaccharide
  • orthogonal protecting groups
Date of Defense 2016-07-20
Availability unrestricted
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.

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