Towards synthesis of biologically important phosphate analogues: exploring H-phosphonate and C-phosphonate chemistry
1999 (English)Doctoral thesis, comprehensive summary (Other academic)Alternative title
This thesis is based on studies directed towards the development of methods for the preparation of phosphorus containing natural products, with the focus on C-phosphonate nucleic acid analogues.
Mechanistic studies concerning formation of the phosphorus-carbon bond resulted in development of two efficient protocols for the synthesis of C-phosphonates from the corresponding H-phosphonate derivatives. These were applied, inter alia, to the synthesis of a novel type of nucleotide analogue containing the 4-pyridylphosphonate internucleotide bond. Also, synthesis of new nucleoside 5'-methylenephosphonate building blocks, suitable for incorporation into oligonucleotides or their conjugates, and a new method for the preparation of alkyl H-phosphonates, are discussed. Finally, mechanistic investigations related to C-phosphonates formation via N->C phosphorus migration in certain complexes of DBU with chlorophosphates, are presented.
Place, publisher, year, edition, pages
Stockholm: Stockholm University , 1999. , 51 p.
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-64034ISBN: 91-7153-933-6OAI: oai:DiVA.org:su-64034DiVA: diva2:454411
Letsinger, Robert, Professor
Härtill 7 uppsatser 2011-11-072011-11-072011-11-07Bibliographically approved