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

Abstract

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 ºC, N -triphosphoryl hydroxyproline (P 3 -( N )-Hyp) was synthesized. An intramolecular attack of carboxyl group on a phosphorus atom of P 3 -( N )-Hyp yields cyclic phosphate derivative (P 1 -( N , O )-Hyp). Hydrolysis of cyclic phosphate derivative occurs simultaneously to form N -phosphoryl hydroxyproline (P 1 -( N )-Hyp). Here, we were able to show that Hyp reacts with P 3m to form the intermediates (P 3 -( N )-Hyp and (P 1 -( N , O )-Hyp) and give the final product (P 1 -( N )-Hyp). The optimum condition for P 1 -( N )-Hyp was Hyp : P 3m = 2(1.0 M) : 1(0.5 M), pH 13, and 25 ºC. P 1 -( N )-Hyp was synthesized by dissolving Hyp and P 3m in H 2 O under the optimum conditions for 7 days, and isolated by adding 2-propanol to the reaction solution. The moisture retention of P 1 -( N )-Hyp and Hyp alone were compared by measuring amount of water. The moisture retention of the P 1 -( N )-Hyp can be increased more effectively than that of Hyp alone.