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Novel Reaction of Linear Phosphates with cyclo -Phosphate in Coacervate

Phosphorus pentaoxide, and various organic phosphorus compounds have been used as phosphorylating agents for organic and bioorganic compounds. Feldmann reported that phosphorylation of alkylamines1 and alcohols2 can be effected by the use of cyclo-triphosphate (P3m). Rabinowitz reported that amino acids (glycine and alanine) condense to form oligopeptides in the presence of polyphosphate or P3m. Recently, we found that some linear phosphates were characteristically formed through the decomposition processes of P3m in coacervate. The contents of various linear phosphates formed were affected by coexistent metal ions, the fraction of water/organic solvent, standing time, and so on. As a part of our developmental work on the application of P3m as a phosphorylating agent, the present authors investigated the reaction of P3m or other cyclo-phosphates with a metal ion and phosphate in coacervate. The formation mechanisms were also discussed from the viewpoint of ring-opening of cyclo-triphosphate and stability of the resulting product in coacervate. The favorable metal ions to ring-opening were Mg2+, Co2+, and Ni2+ ions. However, Mg2+ ion acted as a hydrolysis agent of cyclo-triphosphate and linear phosphates, resulted in the disappearance of selective formation of linear phosphates. The proposal reaction mechanisms in coacervate were shown as follows: