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 (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 (P1-(
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°C. P
1-(
N)-Hyp was synthesized by dissolving Hyp and P
3m in H
2O 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.
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