1623-22-9Relevant academic research and scientific papers
Mild and Chemoselective Phosphorylation of Alcohols Using a Ψ-Reagent
Ociepa, Micha?,Knouse, Kyle W.,He, David,Vantourout, Julien C.,Flood, Dillon T.,Padial, Natalia M.,Chen, Jason S.,Sanchez, Brittany B.,Sturgell, Emily J.,Zheng, Bin,Qiu, Shenjie,Schmidt, Michael A.,Eastgate, Martin D.,Baran, Phil S.
supporting information, p. 9337 - 9342 (2021/10/01)
An operationally simple, scalable, and chemoselective method for the direct phosphorylation of alcohols using a P(V)-approach based on the Ψ-reagent platform is disclosed. The method features a broad substrate scope of utility in both simple and complex settings and provides access to valuable phosphorylated alcohols that would be otherwise difficult to obtain.
One-pot synthesis of organophosphate monoesters from alcohols
Lira, Lucas M.,Vasilev, Dimitar,Pilli, Ronaldo A.,Wessjohann, Ludger A.
, p. 1690 - 1692 (2013/04/10)
A one-pot procedure for the phosphorylation of alcohols provides the corresponding phosphate monoesters in improved yields. The protocol features the use of tetrabutylammonium hydrogen phosphate and trichloroacetonitrile, followed by purification of the crude product by flash chromatography on silica gel. The final step, cation exchange chromatography, affords the organophosphates as ammonium salts that are usually required for biochemical applications. The mechanism appears to be phosphate rather than alcohol activation by trichloroacetonitrile.
Regioselective phosphorylation of carbohydrates and various alcohols by bacterial acid phosphatases; probing the substrate specificity of the enzyme from Shigella flexneri
Van Herk, Teunie,Hartog, Aloysius F.,Van Der Burg, Alida M.,Wever, Ron
, p. 1155 - 1162 (2007/10/03)
Bacterial non-specific acid phosphatases normally catalyze the dephosphorylation of a variety of substrates. As shown previously the enzymes from Shigella flexneri and Salmonella enterica are also able to catalyze the phosphorylation of inosine to inosine monophosphate and D-glucose to D-glucose 6-phosphate (D-G6P) using cheap pyrophosphate as the phosphate donor. After optimization high yields (95%) are achieved in the latter reaction and we show here that it is possible to use these enzymes in a preparative manner. This prompted us to investigate by using 31P NMR and HPLC also the phosphorylation of a broad range of carbohydrates and alcohols. Many cyclic carbohydrates are phosphorylated in a regioselective manner. Non-cyclic carbohydrates are phosphorylated as well. Phosphorylation of linear alcohols, cyclic and aromatic alcohols is also possible. In all cases the acid phosphatase from Shigella prefers a primary alcohol function above a secondary one. We conclude that these enzymes are an attractive alternative to existing chemical and enzymatic methods in the phosphorylation of a broad range of compounds.
Phosphorylation with Pyrophosphoric Acid
Yamaguchi, Hachiro,Ogura, Fumio,Otsubo, Tetsuo,Ikeura, Yasuhiro
, p. 1891 - 1892 (2007/10/02)
Dihydrogenphosphates of primary and secondary aliphatic alcohols as well as phenol were prepared by a very simple procedure with pyrophosphoric acid. t-Butyl and benzyl dihydrogenphosphates could be obtained by a slight modification of the reaction conditions.For the purpose of phosphorylation pyrophosphoric acid was more reactive than orthophosphoric acid.
