Towards synthesis of D-tagaturonate

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Title: Towards synthesis of D-tagaturonate
Author: Viitaja, Tuomo
Contributor: University of Helsinki, Faculty of Science
Publisher: Helsingin yliopisto
Date: 2019
Language: eng
Thesis level: master's thesis
Degree program: Kemian ja molekyylitieteiden maisteriohjelma
Master's Programme in Chemistry and Molecular Sciences
Magisterprogrammet i kemi och molekylära vetenskaper
Specialisation: ei opintosuuntaa
no specialization
ingen studieinriktning
Discipline: none
Abstract: 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.
Subject: carbohydrates
fungal metabolites
synthetic chemistry
protecting groups

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