Studies on pyrophosphates. Part III. A new method for the synthesis of nucleotide coenzymes by means of di-n-butylphosphinothioyl bromide

Abstract

Di-n-butylphosphinoyl bromide reacts with nucleotides to afford the corresponding nucleoside phosphoric di-n-butylphosphinothioic anhydrides in almost quantitative yields. These mixed anhydrides are stable even in the presence of water, but in the presence of silver salts they react readily with phosphoric acid, pyrophosphoric acid, or nucleotides to give the corresponding nucleoside di- and tri-phosphates, or nucleotide coenzymes in high yields, respectively. In the absence of the phosphates, the mixed anhydrides react with silver nitrate to form the corresponding nucleoside 3′,5′-cyclic phosphates in high yields.