N-donor Base Adducts of P2O5 as Diphosphorylation Reagents

25 June 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Donor-stabilized adducts of the P2O5 molecule are reported. The compounds are of the general formula P2O5D2, where D = DABCO, pyridine, and DBU. The DABCO adduct was initially prepared from trimetaphosphate but could be prepared more conveniently from phosphorus pentoxide. The reactions leading to P2O5D2 (D = DABCO) also generate P3O8D3 and both adducts were structurally characterized. The pyridine adduct P2O5D2 (D = pyridine) was most easily prepared in good purity and yield and thus its diphosphorylation chemistry was developed. Its reaction with protic nucleophiles MeOH and HNEt2 yield salts of [P2O7Me2]2-, a dimethyl ester of pyrophosphate, and [P2O5(NEt2)2]2-, a phosphoramidate derivative which was structurally characterized. Diphosphorylation of adenosine monophosphate yielded a cyclic intermediate which could be opened by nucleophiles including water to provide ATP, diethylamine to provide γ-diethylamino-ATP, and uridine monophosphate to provide adenosine uridine tetraphosphate. Adenosine diphosphate was diphosphorylated to provide, following hydrolytic ring opening, adenosine tetraphosphate.


nucleotide synthesis


Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.