New general synthesis of organophosphorus P–F compounds via reaction of azolides of phosphorus acids with acyl fluorides: novel route to 2-deoxynucleosidyl phosphorofluoridates and phosphorodifluoridates

Synthesis and chemical and enzymatic reactivity of thymidine 3′-O- and 5′-O-phosphorofluoridothioates

“…Spleen and sv PDE-assisted hydrolysis of P-F bonds in compounds 3 and 4 is in agreement with earlier findings 12,13 that these enzymes split nucleoside 3A-O-or 5A-Ophosphorofluoridate, respectively, giving rise to the appropriate nucleoside phosphates. From this perspective our data on enzymatic hydrolyses of 3 and 4 disagree with the results of Dabkowski et al, 17 who characterized thymidine 3A-O-phosphorofluoridate as the product of spleen PDE-assisted degradation of thymidin-3A-yl 2A-deoxyadenosin-5A-yl phosphorofluor-idate. Adenosine 5A-O-phosphorofluoridate was found as the product of sv PDE-assisted hydrolysis of the same substrate.…”

Studies on enzymatic hydrolysis of thymidin-3′-yl thymidin-5′-yl phosphorofluoridates and the corresponding phosphorothiofluoridates

“…In this respect, the cleavage of the P-O bond in dinucleoside 3A,5A-phosphorofluoridates (N PF NA) by spleen phosphodiesterase (spleen PDE) and snake venom phosphodiesterase (sv PDE), as reported recently in several papers by Dabkowski et al, 2 attracted our attention. Both enzymes are known as phosphodiester hydrolases that cleave oligonucleotides with natural 3A-5Aphosphodiester linkages to produce the corresponding nucleoside 3A-or 5A-phosphates.…”

Synthesis of [14C] Sarin

“…The disadvantage of the toxicity of hydrogen fluoride was compensated by the practical advantages and the fact that even more toxic substances are produced in the next step which meant that safety measures had to be taken anyway. Alternative methods were considered and among them a method which used benzoyl fluoride and imidazole 8 was studied, but the simplicity of using hydrogen fluoride made it our first choice as fluorinating agent.…”