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Title: A supported phosphorylation reagent for the synthesis of triphosphates and prodrugs
Author: Bruckler, Carole
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2006
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A solid-supported phosphorylation reagent was developed, based on Ludwig-Eckstein chemistry. Different resin supports were evaluated and microporous polystyrene with 1% crosslinking was found to give the best results. The supported reagent was characterised by 31P Gel-phase NMR and phosphorous content and applied to the synthesis of DNA triphosphates. The triphosphates were isolated in 28-50% yields, often without the need for ion exchange chromatography, using preparative HPLC for purification. Propargylamino linked triphosphates were also prepared using this approach. The reagent was successfully applied to the synthesis of a fluorescein labelled Thymidine triphosphate. Using the supported reagent, complete phosphitylation of the alcohol could be demonstrated. The product was isolated by preparative HPLC and its identity proven by 31P NMR and mass spectrometry. Additionally, the reagent’s potential as a handle to access different phosphorylated compounds, such as mono-H-phosphonate esters, phosphate diesters, phosphate trimesters and diphosphoramidates was explored and its application to the synthesis of nucleoside prodrugs is discussed.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available