dc.creator | Keith, Donnan Jamin | |
dc.date.accessioned | 2020-08-22T20:52:50Z | |
dc.date.available | 2019-08-30 | |
dc.date.issued | 2019-08-30 | |
dc.identifier.uri | https://etd.library.vanderbilt.edu/etd-08252019-215206 | |
dc.identifier.uri | http://hdl.handle.net/1803/14015 | |
dc.description.abstract | Zwitterionic polysaccharides (ZPS) activate T-cell-dependent immune responses by major histocompatibility complex class II presentation. Herein, we detail a review of the field of ZPSs and report the first synthesis of a Morganella morganii ZPS (MM-ZPS) repeating unit as an enabling tool in the synthesis of novel ZPS materials. The repeating unit incorporates a 1,2-cis--glycosidic bond; the problematic 1,2-trans-galactosidic bond, Gal-β-(1→3)-GalNAc; and phosphoglycerol and phosphocholine residues which have not been previously observed together as functional groups on the same oligosaccharide. Three unique synthetic campaigns to achieve synthesis of the MM-ZPS are examined within the text; highlighting trials and tribulations of each. The successful third generation approach leverages a first in class glycosylation of a phosphoglycerol functionalized acceptor. To install the phosphocholine unit, a highly effective phosphocholine donor was synthesized. | |
dc.format.mimetype | application/pdf | |
dc.subject | carbohydrate | |
dc.subject | carbohydrate synthesis | |
dc.subject | glycobiology | |
dc.subject | glycochemistry | |
dc.subject | glycosylation | |
dc.subject | carb | |
dc.subject | carbohydrate | |
dc.subject | synthetic chemistry | |
dc.subject | synthesis | |
dc.subject | zwitterionic polysaccharide | |
dc.subject | zwitterionic polysaccharide repeating unit | |
dc.subject | total synthesis | |
dc.title | Total Synthesis of the Morganella Morganii Zwitterionic Polysaccharide Repeating Unit | |
dc.type | dissertation | |
dc.contributor.committeeMember | Craig W. Lindsley | |
dc.contributor.committeeMember | Jeffrey N. Johnston | |
dc.contributor.committeeMember | Brian O. Bachmann | |
dc.type.material | text | |
thesis.degree.name | PHD | |
thesis.degree.level | dissertation | |
thesis.degree.discipline | Chemistry | |
thesis.degree.grantor | Vanderbilt University | |
local.embargo.terms | 2019-08-30 | |
local.embargo.lift | 2019-08-30 | |
dc.contributor.committeeChair | Steven D. Townsend | |