Background and overview[1]
Phosphothreonine is mainly used in scientific research.
Preparation[1]
The combined chemical equation of phosphothreonine is:
Add phosphorus oxychloride (POCl3) (93.6ml or 1.0 mol) dropwise to H2O (36ml or 2.0 mol) under stirring over 1 hour. The solution was stirred and HCl was allowed to grow for an additional hour. Then, 12 grams (0.1 mol) of D,L-threonine was added to the solution over 30 minutes. An additional 30 minutes is required to dissolve any added threonine. After all the threonine has dissolved, place the solution in a water bath at 60°C for 6 hours. The ee value of the D, L mixture is 0. After this time, the solution was extremely foamy and no further release of HCl was observed. To quench the reaction, 14.4 ml (0.8 mol) water was added. Add the water slowly as quite a bit of heat is being generated. Next, add 60 ml of 1NHCl to hydrolyze the polyphosphate, and then place the solution in a boiling water bath for 20 minutes.
After cooling, add 300ml EtOH within 10 minutes, then add 60ml Et2O. Keep the solution in the refrigerator overnight. The next day, the precipitate formed was filtered off, washed with ethanol and ether, and then dried in a desiccator under reduced pressure. The crude weight of the precipitate was 17.1 g, and the crude yield was 85%. Ninhydrin assay yielded 84 mol% threonine and phosphothreonine. Phosphothreonine determination (enzymatic hydrolysis) yielded 85 mol% phosphothreonine. Therefore, there is no significant threonine impurity. Most impurities are attributed to inorganic phosphates. Since the crude precipitate contains almost no amino acids acting as the antioxidant, the prepared solution does not require further purification. Phosphothreonine was recrystallized by the following steps. Dissolve the crude precipitate in boiling water, and add 20 ml H2O per gram of crude precipitate. The solution was cooled and filtered, then 5 ml EtOH/g crude precipitate was added. Yields are typically about 60%. The purity of recrystallized phosphothreonine is 97-99%, with the remainder being inorganic phosphate.
Apply[2-3]
1) For inhibiting off-flavors in oral compositions such as foods, beverages and medicines, and also relates to oral and pharmaceutical compositions containing off-flavor compounds, wherein the oral and pharmaceutical compositions are prepared by adding phosphorylated amino acids (such as Phosphotyrosine, phosphoserine, phosphothreonine and their mixtures) to inhibit odor.
2) Prepare a class of compounds containing the peptide sequence (X-Y-Z)n, where X is an amino acid selected from aspartic acid, glutamic acid, asparagine, alanine and glutamine, and Y and Z are Amino acids selected from alanine, serine, threonine, phosphoserine, phosphothreonine and their derivatives. These compounds have the property of specifically and tightly binding to calcified surfaces, making them suitable for a variety of uses including remineralizing tooth and bone surfaces, diagnosing bone and tooth defects, treating bone and tooth defects and analyzing the presence of calcific deposits in vitro and in vivo and sites, and for industrial, synthetic, medical, dental and research uses where calcification needs to be identified, located or treated.
Main reference materials
[1] US4659671Enzymaticseparationofracemicmixturesofhydroxycompounds
[2] CN97197342.3 Method for inhibiting odor in oral compositions
[3] CN200680035799.1 Calcium binding
