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Browsing by Subject "carbohydrates"

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  • Synthesis of glycoconjugates for Boron Neutron Capture Therapy 
    Matović, Jelena (2019)
    Boron Neutron Capture Therapy is a binary cancer treatment based on the nuclear capture and fission reaction which occur when 10B is irradiated with low energy thermal neutrons. BNCT has throughout the years shown noticeable clinical results with the boron delivery agents that are currently available for testing. However, these delivery agents display deficiencies on multiple frontiers. My goal was to synthesize three different carbohydrate delivery agents for BNCT. Carbohydrate delivery agents have great potential for multiple reasons. They have low toxicity, high aqueous solubility and a high amount of boron atoms can be attached to a single molecule. These three synthesized molecules, 6-O-o-carboranylmethyl-D-glucopyranose, (O)-carboranylmethyl -D-glucopyranoside, (O)-carboranylmethyl -D-glucopyranoside, consist out of a glucose moiety and a carborane cage at both anomeric positions 1 as well as position 6. The synthetic pathways developed were 5-6 steps long and the overall yields varied between 13-15%. The synthesized molecules are currently undergoing biological evaluation.
  • Towards synthesis of D-tagaturonate 
    Viitaja, Tuomo (2019)
    Concerns about the state of the environment and the global climate change has created a need for more efficient and greener ways to produce chemicals and fuels. One solution to these challenges is to find improved ways of utilizing biomass. This thesis deals with the valorization of pectin rich biomasses. Bioengineering yeast to express the alternative galacturonic acid catabolism pathway opens up an opportunity to use these underutilized biomasses in a more efficient way. In order to bioengineer yeast, understanding of the metabolic pathways and the enzymes functioning on these pathways is required. In order to map out certain degradation steps, access to non-commercial compounds and structural analogues is a necessity. The aim of this thesis was to develop a synthetic route to D-tagaturonate, and its structural analogues, which are intermediates on the galacturonic acid catabolism pathway. The chosen multistep synthetic route to D-tagaturonate proved to be challenging. The end product was not obtained, however, the laboratory work showed that the synthetic route is feasible after some minor adjustments. On a general level, new information on the limitations of widely utilized protective groups could be uncovered. These findings will help to optimize the synthetic route to D-tagaturonate. In addition, these findings show that there is still room for improvement in orthogonal protective group strategies applicable to the synthesis of complex organic molecules such as carbohydrates.

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