Peroxide-Mediated Release of Organophosphates from Boron-Containing Phosphotriesters: A New Class of Organophosphate Prodrugs.
Brittany M KlootwykAmy E RyanArbil LopezMitchell J R McCloskeyChasity P JanoskoAlexander DeitersPaul E FloreancigPublished in: Organic letters (2023)
Phosphate mono- and diesters can be liberated efficiently from boryl allyloxy (BAO) and related phosphotriesters by H 2 O 2 . This protocol was applied to the release of a phosphorylated serine derivative and the nucleotide analogue AZT monophosphate. Nucleotide release in the presence of ATP and a kinase provides a diphosphate, demonstrating that this method can be applied to biological processes.