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DNA-based catalytic asymmetric allylic substitution

Kroezen, B. (2010) DNA-based catalytic asymmetric allylic substitution. Bachelor's Thesis, Chemistry.

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In this project a ligand was synthesized, that is suitable to interact with DNA and at the same time is able to coordinate iridium(I). The ligand was obtained by a parallel synthesis of a diene functionality, that is able to coordinate iridium(I) and an acridine moiety, which is known as an intercalator. Both parts were coupled in the last step. Many difficulties were experienced during the synthesis. Diene containing moieties are found to be unstable under strong acidic environments, high temperatures and light. Acridine containing functionalities can degrade to acridone by means of a hydrolysis reaction. This can occur both in the presence of acid and base. The ligand was not obtained pure, but it is believed that the impurity, mainly acridone, can be removed using column chromatography. The catalyst system is expected to be able to catalyze allylic substitutions, where the chirality of DNA is transferred to the products of the reaction, resulting in an enantiomeric excess.

Item Type: Thesis (Bachelor's Thesis)
Degree programme: Chemistry
Thesis type: Bachelor's Thesis
Language: English
Date Deposited: 15 Feb 2018 07:44
Last Modified: 15 Feb 2018 07:44

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