3762-27-4Relevant academic research and scientific papers
Lipid-mimicking phosphorus-based glycosidase inactivators as pharmacological chaperones for the treatment of Gaucher's disease
Clarke, Lorne,Overkleeft, Hermen S.,Robinson, Kyle,Santana, Andrés G.,Scherer, Manuel,Withers, Stephen G.,Zhou, Steven
, p. 13909 - 13913 (2021/11/04)
Gaucher's disease, the most prevalent lysosomal storage disorder, is caused by missense mutation of the GBA gene, ultimately resulting in deficient GCase activity, hence the excessive build-up of cellular glucosylceramide. Among different therapeutic strategies, pharmacological chaperoning of mutant GCase represents an attractive approach that relies on small organic molecules acting as protein stabilizers. Herein, we expand upon a new class of transient GCase inactivators based on a reactive 2-deoxy-2-fluoro-β-d-glucoside tethered to an array of lipid-mimicking phosphorus-based aglycones, which not only improve the selectivity and inactivation efficiency, but also the stability of these compounds in aqueous media. This hypothesis was further validated with kinetic and cellular studies confirming restoration of catalytic activity in Gaucher cells after treatment with these pharmacological chaperones.
Palladium-catalyzed phosphorylation of benzyl ammonium triflates with P(O)H compounds
Chen, Tieqiao,Huang, Tianzeng,Liu, Long,Wang, Wenqi,Wang, Yuan,Xu, Hanshuang,Xu, Kaiqiang
, (2020/03/03)
A palladium-catalyzed phosphorylation of benzyl ammonium triflates with P(O)H compounds has been developed. Various benzylphosphorus compounds were produced in good to excellent yields with high functional group tolerance. All the three kinds of hydrogen phosphoryl compounds, i.e. H-phosphonates, H-phosphinates and secondary phosphine oxides, were applicable to this reaction. The successful scale-up experiment and one-pot synthetic operation also well demonstrated its practicality.
Copper-catalyzed synthesis of alkylphosphonates from H-phosphonates and N-tosylhydrazones
Miao, Wenjun,Gao, Yuzhen,Li, Xueqin,Gao, Yuxing,Tang, Guo,Zhao, Yufen
, p. 2659 - 2664 (2013/01/15)
A new catalytic system for the alkylation of H-phosphonates and diphenylphosphine oxide with N-tosylhydrazones has been developed. In the presence of copper(I) iodide and base, H-phosphonates react with N-tosylhydrazones to afford the corresponding coupled alkylphosphonates in good to excellent yields without any ligands. Alkylphosphonates can also be prepared in a one-pot process directly from carbonyl compounds without the isolation of tosylhydrazone intermediates.
The Michaelis-Becker reaction in phosphonium and imidazolium ionic liquids
Vu, Anh P.,Shaffer, Erika A.,Byington Congiardo, Laura K.,Knight, D. Andrew
experimental part, p. 1845 - 1849 (2010/11/02)
The Michaelis-Becker reaction was performed in imidazolium ionic liquids using sodium hydroxide as base or sodium dialkylphosphites with good yield and selectivities. The analogous reaction performed in phosphonium ionic liquids resulted in decomposition to phosphine oxides. Copyright
Mild and efficient Cs2CO3-promoted synthesis of phosphonates
Cohen, Richard J.,Fox, Daniel L.,Eubank, Jarrod F.,Salvatore, Ralph Nicholas
, p. 8617 - 8621 (2007/10/03)
A mild and convenient synthesis for phosphonates using cesium carbonate (Cs2CO3), tetrabutylammonium iodide (TBAI) and DMF was developed at room temperature. Numerous dialkyl phosphites were screened using a diverse array of alkyl halides and these reaction conditions were found to be highly efficient producing various phosphonates exclusively in moderate to high yields.
