46207-73-2Relevant academic research and scientific papers
METAL-FREE DIRECT ARYLATION OF DIALKYL PHOSPHONATES FOR THE SYNTHESIS OF MIXED ALKYL ARYL PHOSPHONATES
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Paragraph 00449, (2019/02/15)
Provided herein are phosphates, thiophosphates, phosphonates, and phosphinates, methods of making same, and methods of using these compounds and methods for the generation of pharmaceutically relevant phosphate, phosphonate, and phosphinate analogs. This
Reactive cyclic intermediates in the ProTide prodrugs activation: Trapping the elusive pentavalent phosphorane
Procházková, Eli?ka,Navrátil, Rafael,Janeba, Zlatko,Roithová, Jana,Baszczyňski, Ond?ej
supporting information, p. 315 - 320 (2019/01/10)
Nucleotide prodrugs (ProTides) based on phosphate or phosphonate compounds are potent and successfully marketed antiviral drugs. Although their biological properties are well explored, experimental evidence on the mechanism of their activation pathway is still missing. In this study, we synthesized two ProTide analogues, which can be activated by UV light. Using 31P and 13C NMR spectroscopy with in situ irradiation, we followed the ProTide activation pathway in various solvents, and we detected the first proposed intermediate and the monoamidate product. Furthermore, we used mass spectrometry (MS) coupled with infrared spectroscopy in the gas phase to detect and to characterize the elusive cyclic pentavalent phosphorane and cyclic acyl phosphoramidate intermediates. Our combined NMR and MS data provided the first experimental evidence of the cyclic intermediates in the activation pathway of ProTide prodrugs.
Substrate and stereochemical specificity of the organophosphorus acid anhydrolase from Alteromonas sp. JD6.5 toward p-nitrophenyl phosphotriesters
Hill, Craig M.,Wu, Feiyue,Cheng, Tu-Chen,Defrank, Joseph J.,Raushel, Frank M.
, p. 1285 - 1288 (2007/10/03)
The enzyme OPAA hydrolyzes p-nitrophenyl phosphotriesters bearing substituents at the phosphorus center ranging in size from methyl to phenyl. The enzyme exhibits stereoselectivity toward the hydrolysis of chiral substrates with a preference for the S(P)
Mg2+-Promoted P-O vs. S-O Bond Cleavage in the Alcoholyses of Phenyl Phosphatosulfate
Eiki, Toshio,Negishi, Shin-ichi,Izumi, Mitsunori,Ishida, Naoko,Hada, Hiroshi
, p. 2931 - 2935 (2007/10/02)
In order to obtain insight into the selectivity of Mg2+ at the site of bond cleavage of P-O and S-O of the P-O-S linkage, metal ion-promoted alcoholyses of phenyl phosphatosulfate were studied.Mg2+ quantitatively promoted P-O bond cleavage in the methanolysis, but mixed cleavage of the P-O bond, which occurred partly due to hydrolysis by trace water and the S-O bond in the reaction of ethanol, 1- or 2-propanol.The ratio of the S-O bond cleavage against the mixed cleavage increased in a order EtOH (11.5percent) 2+ and Zn2+ promoted selective P-O and S-O bond cleavage, respectively, in the reaction of 2-propanol as well as methanolysis.The medium-dependent change in the selectivity of Mg2+ at the site of bond cleavage was discussed.
