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A Convergent Route to Enantiomers of the Bicyclic Monosaccharide Bradyrhizose Leads to Insight into the Bioactivity of an Immunologically Silent Lipopolysaccharide
Download2019-01-27
Claude Larrivée Aboussafy, Lotte Bettina Anderson Gersby, Antonio Molinaro, Mari-Anne Newman, Todd L. Lowary
The synthesis of bradyrhizose, the monosaccharide component of the lipopolysaccharide O-antigen of the nitrogen-fixing bacteria Bradyrhizobium sp. BTAi1 and sp. ORS278, has been achieved in 25 steps in an overall yield of 6% using myo-inositol and ethyl propiolate as the starting materials. The...
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Development and Application of Protected Amino Acids for the Installation of Stable Post-translational Modifications Using Solid-Phase Peptide Synthesis
DownloadFall 2022
This thesis describes the synthesis of non-canonical amino acid building blocks and their use in solid-phase peptide synthesis (SPPS) to explore peptidic drug analogues based on natural products. We replaced sensitive functionalities found in the structure of naturally produced peptides with...
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2020-01-07
SSHRC KSG awarded 2020: For this project, we will generate three scoping reviews to examine health-related exposure to extreme events like heat waves, wildfires, floods, drought, and air pollution; populations' sensitivity to these exposures; and the adaptive capacity of systems, institutions,...
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Fall 2014
The five-membered carbocycle is a structural motif found in a plethora of natural products and bioactive compounds. The Nazarov reaction has emerged as an effective method to synthesize cyclopentenones and acts as a tool for adding structural complexity to molecular frameworks. This dissertation...
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Fall 2015
Organic chemistry has its foundations in the 19th century; since, it has grown into a number of industries affecting our daily lives such as the manufacture of goods and life saving pharmaceuticals. The need for new and increasingly efficient synthetic methods has grown in response to the...
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Seven- and Eight-Membered Ether Formation via Sulfonium Ylide Rearrangement Processes and Application in an Approach to (+)-Laurencin
DownloadSpring 2010
Given the large number of biologically active natural products containing medium-sized ether motifs, many organic chemists have shown great interest for developing new methodologies to access these structures. In particular, numerous synthetic methodologies for the construction of seven-membered...
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Synthesis of Biobased Polyethers, Polyesters and Polyamides from Canola Oil Derived Monomers Using Microwave Irradiation
DownloadSpring 2021
Polymers are essential in modern life’s sustainable growth with their diverse applications in packaging, construction, automotive, electronic industries, etc. Nowadays, polymer industry mainly depends on petroleum resources as feedstock and energy source. Increased environmental concerns and...
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Synthesis, Structure and Properties of a Novel “Frustrated” Benzoxaborole and the Role of Boron in Bioconjugation
DownloadSpring 2020
Chapter 2 describes an optimized 7-step successful synthesis of a first of its kind permanently open-form ortho-hydroxyalkyl arylboronic acid, otherwise known as a “frustrated benzoxaborole”, with a columnless purification and complete structure elucidation. This novel compound is completely...
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Synthesis, structures and reactions of hydrotris(pyrazolyl)borate complexes of divalent and trivalent lanthanides
DownloadFall 2009
The synthesis and reactions of hydrotris(pyrazolyl)borate, (TpR,R′) supported ytterbium(II) borohydride and lanthanide(III) dialkyl (Ln = Yb, Lu) complexes were investigated. The lanthanide(III) dialkyl complexes were found to undergo both hydrogenolysis reaction and protonolysis reaction with...