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Synthesis of Chlorovirus PBCV-1 N-Glycan Analogs

  • Author / Creator
    Byers, Brock W
  • Chloroviruses are a group of water-borne viruses that infect eukaryotic, chlorella-like green algae. Unlike most other viruses, chloroviruses come equipped with their own carbohydrate-processing enzymes; they do not rely on the host’s biosynthetic machinery for glycoprotein assembly. Chloroviruses express a set of unique N-linked glycans, which, at their core, contain a conserved pentasaccharide comprised of a highly branched fucose residue situated on an uncommon β-glucose residue that is N-linked to asparagine.This thesis will focus on the synthesis of six N-glycan analogs from the chlorovirus PBCV-1, for their use as probes in the viral N-glycan biosynthetic pathway. Three of the target structures are derived from truncated N-glycans expressed by antigenic PBCV-1 mutants while the additional three are putative biosynthetic intermediates. The six structures range from tetra- and pentasaccharides to a highly branched hexasaccharide. Each structure was successfully accessed from a core α-ʟ-Fucp-(1→3)-[β-ᴅ-Xylp- (1→4)]-β-ᴅ-Glcp trisaccharide using a linear synthetic approach. The strategy hinged on the use of orthogonal protecting groups on the central fucose residue to assemble the branched structures

  • Subjects / Keywords
  • Graduation date
    Fall 2021
  • Type of Item
    Thesis
  • Degree
    Master of Science
  • DOI
    https://doi.org/10.7939/r3-046x-w142
  • License
    This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for non-commercial purposes. This thesis, or any portion thereof, may not otherwise be copied or reproduced without the written consent of the copyright owner, except to the extent permitted by Canadian copyright law.