Study On Synthesis And Properties Of Phosphoryl Amino Acids

The research shows that phosphoryl amino acids could act as active mini-enzyme for some degree. Obviously the studies on the phosphoryl amino will give help in the process of realizing some life phenomenon, mechanism, and exploring the origin of life. Meanwhile, more and more application prosperities are being shown by phosphoryl amino in their applications to biological technology and medicine fields. In the work described in this paper, two methods for synthesizing 20 kinds phosphorlated amino acids were studied, also the methods for preparation and purification were further improved.Method 1: 20 kinds of phosphoryl amino acids were synthesized by a modified Atherton-Todd method proposed by professor Zhao. Good yield was obtained. The synthesis route is shown below:Method 2: The aim of this study is to find if NaCIO method could be successfully to apply to 20 kinds of phosphoryl amino acid synthesis. In this thesis, 20 kinds of common amino acids were posphorylated for the first time by using diisopropyl phosphite and NaCIO as phosphorylated agents. Good yields were obtained by adding appropriate tetrabutyl ammonium bromide as phase transfer catalyst, and also by adding excessive diisopropyl phosphite to compensate the consumption caused by hydrolysis under basic condition. Meanwhile, the technological conditions of NaCIO method were further deeply studied by orthogonal experiment. The experiment shows that the yields were affected not only by proportion of reaction materials, selection of extraction agent, but also by final acidity of reaction solution for some degree. Finally relatively suitable conditions for production were obtained.1. The structures of all the target products were elucidated and proved by 1H NMR, 13C NMR, 31P NMR, IR, optical rotation and ESI-MS, and also all the relative spectrum data were consummated.2. Three crystals of phosphoryl amino acids were obtained, and their structures were further confirmed by x-ray data,3. Aqueous solutions containing N-diisopropyloxyphosphoryl amino acids (DIPP-AA) and p-cyclodextrin (P-CD) have been analyzed by using electrospray ion trap mass spectrometry (ESI-MS) in conjunction with tandem mass spectrometry (MS/MS). The results suggest that p-CD could catalyze hydrolysisreaction of DIPP-AA to produce free amino acids (AA). DIPP-AA and P-CD could form P-CD/DIPP-AA complex in the aqueous solution. Amino acid resulted in the hydrolysis process were also observed to form the singly charged 1:1 (P-CD/AA) complexes with β-CD. The catalyzed mechanism of hydrolysis reaction was assumed by the results.