PHOSPHORYLATION OF HYDROXYPROLINE WITH TRISODIUM CYCLO-TRIPHOSPHATE AND EVALUATION OF THEIR MOISTURE RETAINING PROPERTY

抄録

Phosphorylation of hydroxyproline (Hyp) has been achieved using inorganic trisodium-cyclo-triphosphate (P_3m) in aqueous solution. In the reaction of Hyp (1.5 M) and P_3m (0.5 M), at pH 11, and 10°C, N-triphosphoryl hydroxyproline (P₃-(N)-Hyp) was synthesized. An intramolecular attack of carboxyl group on a phosphorus atom of P₃-(N)-Hyp yields cyclic phosphate derivative (P₁-(N,O)-Hyp). Hydrolysis of cyclic phosphate derivative occurs simultaneously to form N-phosphoryl hydroxyproline (P₁-(N)-Hyp). Here, we were able to show that Hyp reacts with P_3m to form the intermediates (P₃-(N)-Hyp and (P1-(N,O)-Hyp) and give the final product (P₁-(N)-Hyp). The optimum condition for P₁-(N)-Hyp was Hyp : P_3m = 2(1.0 M) : 1(0.5 M), pH 13, and 25°C. P₁-(N)-Hyp was synthesized by dissolving Hyp and P_3m in H₂O under the optimum conditions for 7 days, and isolated by adding 2-propanol to the reaction solution. The moisture retention of P₁-(N)-Hyp and Hyp alone were compared by measuring amount of water. The moisture retention of the P₁-(N)-Hyp can be increased more effectively than that of Hyp alone.