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Synthesis of a novel nucleic acid mimic: P-boranomethylphosphonate
1Paul M. Gross Chemical Laboratory, Department of Chemistry, Duke University, Durham, North Carolina 27708-0346, USA.
Nucleosides, Nucleotides & Nucleic Acids
|September 21, 2001
Abstract:
A new type of non-ionic nucleotide analogue with a doubly modified internucleotide linkage, P-boranomethylphosphonate, has been successfully synthesized and characterized. Dithymidine boranomethylphosphonate 5 is the first example of a P-boranomethylphosphonate compound; it is a highly lipophilic phosphodiester analog, which is almost totally resistant to both snake venom phosphodiesterase (SVPDE) and bovine spleen phosphodiesterase (BSPDE). P-boranomethylphosphonates are expected to be promising candidates for mechanistic, diagnostic and therapeutic applications.